Dating 101 (as two single ambitious women) - podcast episode cover

Dating 101 (as two single ambitious women)

Feb 12, 20251 hr 4 minSeason 3Ep. 4
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Episode description

Struggling to balance your career goals and quest for real love? Look no further! In this special Tiger Sisters bonus episode, Jean (mid-30s) and Cherie (late-20s) reveal their newly discovered 3-part formula—Stability, “Juice,” and that elusive X-Factor—to help you find (and keep) genuine connection.


Expect raw truths on heartbreak, honest talk about dating apps vs. meeting IRL, and hard-earned lessons about building long term relationships—applicable for both single and coupled people.


Want to make room for both ambition and meaningful romance? Check out this episode and don’t forget to subscribe for more real-life insights!


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🐯🐯👯‍♀️ Tiger Sisters Podcast | Career, Entrepreneurship, and Life


Welcome to Tiger Sisters, your go-to podcast for career mentorship and life guidance! Hosted by Cherie Brooke Luo and Jean Luo, we’re your internet big sisters here to demystify the ups and downs of navigating careers, tech, and entrepreneurship— all while staying healthy, stylish, and joyful along the way.


Cherie is an influencer who has broken down the complexities of big tech, finance, and MBA programs for millions of viewers, with over 100M+ views across platforms. Jean is a tech product executive and investor, holding over 50 AI patents, who has built an impressive career in product management and institutional investment at companies like Goldman Sachs and Snapchat.


Between the two of us, we’ve survived stints at top investment banks and big tech firms, founded startups, and earned four Ivy League degrees—if we’re counting Stanford! Yet, we still find time to focus on wellness, friendships, fashion, and skincare, always sharing the lessons we've learned along the way.


Whether you’re here for career advice, stories about balancing life’s challenges, or just to hear our honest takes on what it means to pursue fun, wealth, and joy in all areas of life, we’ve got you covered.


💛 LET'S CONNECT: 

~ CHERIE ~

🤳🏻 Instagram – https://www.instagram.com/cherie.brooke 

📱 TikTok – https://www.tiktok.com/@cherie.brooke 

✍🏻 My Substack – https://cherieluo.substack.com/ 

👩🏻‍💻 LinkedIn – https://www.linkedin.com/in/cherie-luo/ 


~ JEAN ~

🤳🏻 Instagram – https://www.instagram.com/jeanluo_/

👩🏻‍💻 LinkedIn – https://www.linkedin.com/in/jeanluo 


🎵 Music produced by Sammy Signal https://open.spotify.com/artist/2HsyknHuxhT8RoZfn5rqMS


🛍️ Items Referenced:

🍵Sisters Matcha & SISTERS Merch:www.sistersmatcha.com

✨Tiger Sisters & Friends Japan Trip (May 2025): https://trovatrip.com/trip/asia/japan/japan-with-cherie-luo-may-2025  

♠️ Everything else: https://amzn.to/3z0dx5b


⏰ Timestamps:

00:00:00 Single, Ambitious & Over It? Welcome to Our Dating Dilemmas

00:01:22 Roses & Thorns: Winter Blues and Sonoma Wine Country Magic

00:09:26 Girl Gang Goals: Cherie’s New Founder Besties

00:14:36 Ouch! Cherie’s Golf Injuries & a Goopy Deep Cut

00:17:56 Why Romance Matters as Much as Career Success

00:19:19 Jean’s Heartbreak Confession: 8 Years Down the Drain?

00:24:18 The 3-Part Love Formula: Stability, “Juice,” & the X-Factor

00:33:21 Chemistry vs. Commitment: What Really Lasts?

00:38:58 Jean’s Biggest Lesson: Do Values Actually Align?

00:43:33 The “8 Dates” Book: Why We’re Intrigued…or Terrified

00:51:12 Hinge Confessions: Why Does It Feel Unhinged?

00:56:09 LA vs. SF vs. NYC: Best City for Dating?

00:58:28 Falling for Love Again: The Thrill & The Fear

01:00:12 Holding Hope and Hopelessness at the Same Time

01:02:00 Coming Soon: Egg-Freezing & Deeper Dating Talk

01:02:55 Thanks for Watching—Love You!!

Transcript

Single, Ambitious & Over It? Welcome to Our Dating Dilemmas

What is it like dating as two ambitious women who are single in their late 20s and mid 30s? Gina and I talked about dating in our season one episode of Tiger Sisters, and now we're giving you a dating update and also going to talk more about relationships, how we see dating apps, our formula for dating, happiness and balancing, feeling hopeful and also hopeless while

dating at this age. I'm Shuri, I'm Jean, and we're the Tiger Sisters. With Valentine's Day coming up, we wanted to do this special bonus episode for Season 3. In addition to all of our amazing interviews, we kind of thought we'd interview each other. And this is a very, very highly requested follow up to the earlier dating episode that we had. So excited to get into it. And we'll get started right

after this break. Hey guys, quick break to let you know that we now have merch on Sisters matcha.com. We have sweatshirts and T-shirts that we designed ourselves. Go check it out and please rate US five stars on Spotify and Apple Podcasts. These ratings are so important for the distribution and survival of Tiger Sisters Podcast. Thank you for your support.

Roses & Thorns: Winter Blues and Sonoma Wine Country Magic

OK, so we're going to start off with the roses and thorns. So, Jean, what is your rose and your thorn? OK, I'll start with my thorn. I have been having sort of a bout of SAD seasonal affective disorder or seasonal affective depression. I don't know, disorder I think, but it's basically like the winter Blues, but it's actually clinically, it's the clinical name for winter Blues. And I remember I got it really, really badly back in Boston

seven years ago. And that was part of my calculation for being like, oh, like, I should move to Los Angeles after school. Like the land of where it's only sunny, basically. But this year, this winter. And like, I can't like a little bit down every winter, but this winter with like the, you know, the fires in LA and then just like kind of like running around and everything. And you were sick for a little bit, too. And I was sick. I had pneumonia from the fires.

I just have been feeling kind of like in a funk. So I've been trying to do things to like, get out of it while also not being like too hard on myself. So that's kind of my thorn. So anyone else who goes through who feels like winter Blues or you feel like you're in a funk, I see you. I feel you. You're not alone. We got this. Don't be too hard on yourself. Do things that are like

rejuvenating for you. And then at the same time, like what I'm trying to do is like push myself a little bit to do activities even if I really don't want to 'cause I think that's like one of the underlying feelings of like when you're in the the sad seasonal faction disorder, like period. You just like kind of don't want to do anything. You feel like nesting and resting more. Yeah, like you just feel like like you don't want to do

anything. Like you're like, oh, I can't possibly bring myself to do this. Or like you just feel like kind of like, you know, when you're in your like ludial phase for women out there, when you're like, I cannot for myself to do anything. It's like feeling like that, like all the for many weeks on it. So that is the thorn. Well, you that's also we have bright lights on us to simulate sunlight, which is one of the things that can help. Sad. Yeah, get a happy lamp.

So you're saying I should record more episodes? Jeez. She's trying to put me to work. Maybe. OK, so that's the thorn, but I have a fabulous rose, which is this past weekend, I went up to Sonoma and had an amazing weekend away with four of my girlfriends from HBS. And we basically, like descended upon Sonoma from like I came from LA, my friend came from Texas, one came from New York, and then two of them live in SF.

So like we all like, flew in from like all corners of the United States. And it was just like the most like rejuvenating, like wonderful weekend to like reconnect. Yeah. Like girl time is so special. Actually, one of the things that one of my girlfriends said at the time, she was like, she was like, you know, like women, girlfriends really carry you through life. She's like, yes, there's men, there's partners, there's, you know, you'll have your

boyfriends and your husbands. But she was, like I've always said, like girlfriends carry you through life. That's so Sex in the City. I really is that's. What Charlotte actually said before, she's like, Oh my God, what if we wear each other's Zumba? That's so. Right. And you know, guys are just, you know. There. Yeah, yeah.

So like, not only was it fun and rejuvenating and like really helped me like I almost, I almost, I really like for not a split second, but for a moment in time, I really almost didn't go because I was so like in my sad, I was like, oh, now I have to like take a flight and like go. And like then I was really sad. It was going to be rainy there over the weekend because there, there was an atmospheric river. But it turned out to be wonderful.

And also like, what's crazy is so the group of us like we aren't always in like super close contacts. So like we hadn't been together in person since last May. And what is crazy is how many things like life changing events have happened for all of us in the time between May and now that like February or end of January.

It's like 8 months. Yeah. But I was like shooketh like like major like life changing, like health events, like it like near death health events like like changing of like jobs, like, you know, a changing of relationships, like so many things have happened.

And it's just like, I don't know, it kind of it really gives you perspective in a way to to really share yourself like so, so like deeply and honestly and like tell your friends like your true everything that's going on and like vice versa. It's just like. It's very special. You can be open with a group of women who support you and support you through like my professor Joel Peterson says at Stanford, like he says that it will always, it will rain in

everyone's lives. Like the rain will fall is what he says in everyone's lives. Be that like the death of a family member, a huge health crisis, and you just need to find support systems that will help you get you through the rain. Because he's like, there's nothing else guaranteed except for like rain in your life.

Yeah, well, but it's also, it's also really interesting because like we shared these things with each other, but then also like on the surface, everyone's life looks like amazing. Like if you just were to be like not super close friends, but like friendly with the person, you'd be like Oh my God, like you're. Killing it, so many different ways to do that and not know that like deep down there are these like giant pillars that are changing and impacting them.

Yeah. So yeah, it's not all, like, doom and gloom, but I'm just saying that like, it's really special to be able to, like, share yourself fully with people. And, OK, this is the other thing is that they are all women that I deeply respect on, like, many different levels. And like, I feel like I learned from them. And yeah. And it was also helpful to just go and kind of like plug into. So one of my friends, she lives in San Francisco. And so we, like, stayed at her place in Sonoma.

And it was just also really fun to like, plug into somebody else's life for just a couple days and just like see how they live and almost like learn from them in that way, you know? Yeah, you get to live vicariously. Yeah, a bit to be like, oh, like, I love your interior decoration. Yeah, I love your style.

Yes. Yeah. And it's also nice sometimes I think, for them to, like, see your admiration of them, like reflected, you know, like, you're kind of like mirrors of each other in a way, like real friends. That's so special. Yeah, so it was, I feel like a much, much needed weekend that just so happened to be like at the perfect time. And it was like a really, really good rose to like the thorn. I was really happy you went to Sonoma. And I actually told mom about it too, OK.

And she was. Really, Narc? But and she was really happy that you were going too. Oh, thank you. Yeah. Like it's good for you I feel like to catch up with girlfriend, especially ones that you you hold so dearly. Yeah, yeah, it was really nice. So how about you?

Girl Gang Goals: Cherie's New Founder Besties

What is your relative for? My Rosa is actually similar. OK, yeah, it's not my like old friends, but it's new friends that I've made in LA. We have a group of girlfriends. There's like four of us and we are all the thing that has brought us together is that we are all founders, Co founders of CPG companies. So Gina and I have founded Sisters Matcha, which is our Matcha brand.

We're drinking it right now. You might have heard from an earlier AD that we put in there, but so Jean and I have Co founded Sisters Mancha and then these three other women who are in my like LA girlfriend group are also CPG founders and these three women are brilliant, really special. We have like so much to talk about of course, on the business side because we all respect each other, but we all kind of have different like specialties as well. Like they come from different backgrounds.

One woman is in private equity. Another person used to work at a larger like much larger, like food brand and the last woman has experience working in like beauty, but at like a giant beauty company. So like, it's so interesting how we've come together and I really. And then your tech. And then one was McKinsey. Exactly, Tech McKinsey and then two of the women went to HBS. They recently graduated my year. So we've also bonded and talked about that. And that's actually how I know

one of them. And they're also like super fit, really well adjusted, like go getters and super career driven. So I really respect them as people too. And I've talked to one of the women about like we talked about like dating and guys and like, I can just tell like they also really respect themselves a lot and have a very high bar for. Themselves in all. Aspects of their lives.

And that just makes me respect them even more 'cause, you know, we were kind of talking about boys at at one point and like who this girl's dating and she was just like giving like a very no BS response to be like, Can you believe he did that? And she's like, that's unacceptable actually. And like, I will not tolerate that. You know, I was just like, yes, you know, I love no BS. I love no BS the. Older I get the more I value no BS. Yeah, I, I really appreciate

this group. And then this coming weekend, I'm actually going skiing with one of the women as well who's in who's brought me into her friend group here. And so I, I, I so appreciate that. And it just goes to show the power of female friendship, yes. Well, I was just gonna say, like, the power of female friendship is also there's something really special in, like, the group where it's like you admire each person so much in different ways, but then also it's kind of like reflects on

you as well. It's like you see their beauty and their power and their, like, magnetism and their skills and their kindness. And then it's also a reflection on you. Yeah. It's like it gets all of that goodness is also reflected back to you. That's right.

But it's funny that you were like talking about how amazing this group of girlfriends are because I also have like a newer group of girlfriends in LA that like the the joke that we made when we like first all hung out was like, we are like basically the C-Suite of like a Fortune 500 company. It's funny. They're all like 1 is like a super successful, like lawyer. What?

Like I worked in product. 1 is a product designer, 1 is like a marketing like CMO, like everyone is just hell yeah that has their own lane is like amazing and. Wait a second. Don't start a company with them now because we're doing stuff, but consider it later on, yeah. Yeah, but it was just like a joke that like. Yeah, it was just, that's powerful. Maybe your group chat should be called the C-Suite, although that's like, kind of disgusting in corporate.

But like, you know that Gina and I like that shit. So if you're here watching this, you like it too. So got him. Or you will like it the more episodes you watch. I'm looking at you. OK. Wait, I kind of love this. This episode was meant to be about dating in relationships. And then I love how it's both of our roses were about Galentine's Day. Yeah, and non Valentine's Day. Yeah, yeah, yeah, I do have a Galentine's Day planned.

Oh, so do I Actually, one of the women who's in the group of the four of us is hosting a Galentine's Day. See. Oh, I love that. My girlfriend is flying in from Aspen for or Valentine's Day. Are you guys hanging out on the 14th? I think on the 13th, yes. 13th and 14th. Wait. What are you doing on the 14th? I was thinking about this. Should we do something together? Maybe. Being busy, OK. I'm not going to commit on camera.

Oh my God. All right, I was going to invite you on a date for sushi, but never mind, you're paying.

Ouch! Cherie's Golf Injuries & a Goopy Deep Cut

OK. And then so I'll just wrap up with my thorn. I've had, I don't know if it's like persistent or acute, but I've been having back pain. That is my thorn. She's only 29, ladies and gentlemen. Guys, this is 29 they're. One year early. 30 is coming up so soon and like, Oh my God, in less than six months. Holy shit. Wait, I holy beep. Oh my gosh.

OK, anyways, I have back pain. It was first first started a couple of weeks ago when I was playing golf a little bit too, like the activity was too strenuous. She's playing golf like 3 days in a row. Three days in a row I swing really hard and it was 25 degrees, 29° and then I've been working out a lot, so I've also kind of like strained my back again. She was playing sub freezing golf. Yeah, so I think I need a chill. Yeah. And take it easy. A little easier, no?

Kidding. I've been going to the gym like for 10 days in a row, which I'm really proud of, but I think I need to go a little bit easier and have more rest days, like walk more, stretch more 'cause this is 29 1/2 guys so I need a chill. So that's my thorn and I'm trying not to get injured when I'm going skiing this weekend. So I really, it's like on my mind, you know? So that's my thorn. Yeah, don't be the one loser at Deer Valley. I need I lost half a day of

skiing. That's such a good reference. Does anyone know that reference? That's a reference to when Gwyneth Paltrow had to go to court because she had a collision with another person. I think someone collided into her. Yes, but he still sued her, right? And it was at Deer Valley, and it was like. They're like, what were the losses, man? She's like, ma'am? And she's like, well, I lost half a day of skiing.

But what was iconic is at the very end after the judge ruled in her favor and the man lost, she, I think she was wearing this like, white suit, like a cream blazer. And she like walked up to him at the end and she like, touched his shoulder and like leaned into his ear and like whispered something into his ear. And they walked away really well. Apparently what she said was like, I wish you well or something like that. Like I hope you know you have a good life or something.

I did not know that I have. To look this up now to see exactly what she said interesting. But it was like, it was like a, a kind thing to say, but you know, it could be slightly ominous too. It's. A little bit threatening. It's like, yeah. I wish you well. And, yeah, like, I hope you have a nice life, you know, watch out. You know, the undertones. Anyways, let's dive right into the episode. Yeah. And we'll get into the episode right after this quick break. Hey everyone, quick break to

share something special. Sisters Matcha. We've launched limited batches of ceremonial grade single estate single cultivar matcha straight from the family farm Sheree worked on in Japan. It's pure, authentic, and crafted with intention. Head to Sisters matcha.com to grab yours before it sells out. Make matcha your daily ritual for lasting energy and focus. OK, so welcome back.

Why Romance Matters as Much as Career Success

Wanted to dive right into this episode and give you guys some context. So Gene and I are going to be talking about dating and relationships and romance and all that stuff. But if you've been watching, you know, season 3 of Tiger Sisters, you know our content is usually very professional. In season 3, we're interviewing investors, CEO's, founders, professional people.

Gina and I truly believe that Tiger Sisters represents the whole self like we can talk about our careers, be super driven and ambitious as the title of this, you know, video says, But that also includes how it's going with relationships, both, you know, friendships and romantic. And we want to talk about this more openly with you guys.

It's usually not something that we talk about, but we hope to inspire more conversation around it because it's the conversations we're having with each other and with our girlfriends. Yeah. And I think you guys know that. You know, in the past, I have kind of worked on being more vulnerable and more been for the sake of this podcast. And thank you so much for all the feedback over the last couple seasons in the comments of saying like how me being vulnerable has helped you guys

in certain ways. That's really encouraged me to continue to be open and vulnerable. And also I was even more convinced that we should do this

Jean's Heartbreak Confession: 8 Years Down the Drain?

episode when I saw the most recent Call Her Daddy episode with Rachel Kirkconnell, who was the winner of The Bachelor I think like four or five years ago. And she and her partner Matt just recently broke up after a 4

plus year long relationship. And I didn't watch the whole episode, but I watched some short form videos and snippets of it. And just like through the course of that and like hearing the conversation between Rachel Kirkconnell and Alex Cooper, I just heard her say things that I resonated so strongly with and I had never really heard anyone else say. And she kind of verbalized things. I'll give you an example.

So the strongest example was when she said she was like, yeah, I just felt really sad because I imagined all these, like, future children with Matt. And they were like, all gone. And she was like, I don't know if that, you know, I don't want to sound crazy. And then Alex Cooper jumps and she goes, no, you don't sound crazy at all. And that is something that's like a feeling that I myself have had after the dissolution of my engagement and eight-year

long relationship. Like, you know, that was something that for so long, for all eight years, I had already like conceptualized a life and a future with this person, which included like beautiful in my mind, children, beautiful imaginary children that I had thought about for so many years. And like, it was a kind of like a foregone conclusion. And it was almost in a way like the, you know, the dissolution of that relationship and engagement.

Like it wasn't just the relationship, but it was the entire future life was just like kind of like poof, like up and disappeared, including all of those like imaginary children that I had had in my head for almost a decade. So like hearing her say something so similar and then hearing Alex Cooper be like, no, that doesn't sound crazy. Like that was so powerful. And it really touched me in a way where I was like, these sorts of conversations are

important for us to be having. Like they are pretty much like equally just as important, I think as all of the conversations we have about like career, growth, learning, because, you know, the your life is like a holistic picture. So yeah, I just think that maybe like to some people, these conversations seem trivial or like not as important as the

ones that are more professional. But I have come to the realization that they are just as important because these are all the things that we're going through in life. And that's my soliloquy. Thank you for the yes. I mean honestly, like people say, the most important decision you'll make in your life is who you choose to marry. So I mean, it's the most. Important decision that'll affect your finances, that'll affect, you know, your progeny that'll affect your your progeny and.

It'll. Affect your immediate family it. Affects your daily health because it's the person that you spend the most meals with. Right, your habits too. Like what are their habits? Yeah, if you go to the gym. Yeah, or don't go to the gym, you know, if you guys are more sedentary. I mean, it's just everything becomes so intertwined. So it, it seems natural that we talk about this. But I agree, like I don't know why in society it has become more trivialized or like Zena's

like that's not a serious topic. But like if we're going to talk about it in like kind of an academic way, guys, I bring up a formula. I made a formula. Like I am thinking about it in a much more like structured way. Yeah, I think it gets trivialized because it's considered like a women's topic. And not to say, you know, not to bring up the patriarchy, but. But in the patriarchy.

But the patriarchy sort of like by default trivializes anything that is like considered to be like a women's topic. I mean in a like heterosexual relationship it I mean in every relationship it takes 2 but in a heterosexual relationship. Not in every relationship. Maybe 3? Is that what you're? Getting oh, I was thinking some people say they're self partnered. Oh, never mind. You went down the number, I went up a number. Remember Emma Watson said that a

few years ago? She was like, I'm self partnered. I was like, I think she said that in a Vogue article. That's some bullshit. Just kidding guys. I read Vogue for the articles. Yes. Sure, sure.

The 3-Part Love Formula: Stability, "Juice," & the X-Factor

Like I said, there have been many, many requests for a Part 2 of our dating episode and one of the questions that we got from the mailbag I will read out loud from boarding 711. They asked. I'd love an in depth analysis of what worked and what did not work in past relationships to help inform the future. Great question. That's great question. It's only. Something that I've been thinking about every single day of my life, and now I have a platform to talk about it. Yeah. And so funny.

Actually, after our first dating episode went out, I think there's like, close to like, 15,000 views on that episode. Like a lot of my Stanford friends actually like, messaged me because I think they were like, they wanted the tea. They like wanted the the juicy, the sip. OK, so this is Part 2 of that dating episode. I just thought it was funny. I have been doing a lot of reflecting, especially as, you know, the new year just happened. And I was thinking about like,

what do I want for 2025? I want to be more intentional with dating. And so I've been reflecting on my past relationships and I've come up with a formula for happiness. Roast me in the comments if you'd like or. Provide for dating happiness. Yes, yes for dating happiness, for a relational happiness. Romantic relation happiness. Exactly. First of all, this is personal. Like, I don't know, you guys can listen to it and maybe if you it resonates with you, you can, you

know, adapt it to your life. She said. Results may very This is not my professional opinion. This is my only, you know, my only lived experience, but so I'll give you guys the formula and I also like don't know if a formula is like what you need for love. Like it seems like love and an equation inherently do not mix.

Well, I think it's just for you, it's a, it's helpful as an exercise to have a structured way of thinking about it as opposed to feeling like, I don't know, there could be like 50 million inputs and how do you know what's actually important and what's not important? And this is the way you've come up with this formula is through your experimentation of dating and what you've learned from your past relationships.

And then this is like a very structured way for you to apply your learnings to like summarize and then apply your learnings going forward. It's honestly like guardrails. I feel like because I'm like, I kind of need these things to feel fulfilled and happy in a romantic relationship. So here's the equation. On the other side is happiness. Happiness equals and it's three things that make up this equation. The first thing is stability. Second is what I'm calling juice.

And the third is an X Factor. So stability are all those things that I feel like I need to feel very like safe and cared for and a relationship. And a lot of these things are what some people might call baseline, but I have since like put it a label on it and a name like, OK, these are the things that I need. So I feel like an example of stability is like feeling prioritized, being like considered and decisions picking me up, dropping me off. Like taking the initiative to plan dates.

I want to be thought of when we're not together, showing me that we're thought of. These are like things that make me feel very safe in a relationship, psychologically safe and also physically safe. And I think in my past relationships I had felt not prioritized it. It felt really bad. We had really good chemistry juice, which I'll get it get into, but like, I don't know, I just like didn't feel like they put as much time and energy into the relationship as I was. So that's stability.

Jump in if and if any questions. I'm absorbing OK and juice is I don't know if I need to explain this one. It's just chemistry. It's just like, are you vibing with someone? Are you calling it juice? That's what my therapist called it actually. OK. Like I described it to him and he's just like, that sounds like juice. And I was like, OK, do not like that word. It's unusual, it's memorable. It's memorable. OK. So we'll go with that. Yes, so. Juice, juice.

But honestly, like, I wrote down all the things that are like, juicy to me, and I wanna like, clarify that, like, none of the things that I listed were physical traits. It was all like, very much like, am I intellectually stimulated? Do you have a good sense of humor? Like, do I feel like very connected to you right now? So juice is just attraction. It's attraction. I do think it should include physical attraction though.

Yeah, of course. Yeah. But I guess when I first thought about it like none of the things were about physical attraction, but that needs to be added. I think it's 'cause your definition of being physically attracted to someone is not like so prescriptive, like it's not like they must be brunette or they must be blonde or like anything like that. So I think it's just being

attracted to someone. Yeah, physically attracted, whatever it may be. Humor is a really big part of what I find attractive to, and so having a good sense of humor is definitely part of the juice. And the last is an X Factor, what I'm calling an X Factor. I think even in my. Platonic relationships like my best friends, my best guy friends, best girlfriends have an X Factor about them.

They're just like really interesting people who are passionate about something and they're like a subject matter expert in something because they're just nerds. They like, care about like, running or they care about, you know, mountain biking or about, like content creation, like whatever it is. Like, I think my friends are

just so interesting. And I think dating people who are also interesting and have hobbies and are not just focused about work is something that I've found very stimulating. How are you going to like apply this formula? I'm actually like have already started applying this formula like day-to-day in like my interactions, Like I've gone on like 2 dates and I kind of see where I feel very fulfilled in the formula and where some things are lacking.

And actually last night I went on a date and I didn't tell you this. I mean, I didn't tell you this part, but we actually had a conversation where I felt like part of the stability was lacking with this person because of something they had done on a prior date. And you told them? Well, they had asked me like, so they had asked me like, I don't want to get too many details here. The conversation led to us

talking about it actually. And I was like, oh, I didn't feel so great when this happened actually. And I was like, it's also part of my formula, which I like mentioned, I mentioned it to him so he was familiar and I was like, I didn't feel like super like comfortable She had. Given him a. Rubric. I had given him a rubric and he and graded him against this side. Not exactly. She gave him. She was like, these are the areas in for improvement you will be evaluated against if you

want to be promoted. That's what you gave him. But actually. What is it called when it's like that list of like the document that the promotion write out for promotion like promotion requirements or something like that? Oh my God, you're so right. Oh, it's like we call them career ladders. Yeah, yeah, yeah, yeah. PM ladder or like PM roll or roll ladder, these are all the requirements to get to the next.

Stage. I mean, I wasn't even telling like it's I wasn't even telling him my equation. She's like, it came out really naturally. I wasn't telling him my equation. So like to tell him I was grading him on it. I was just sharing this like new thought that I had. And then later on I was just like, oh, I'm so in my mind. I was like, I'm so happy I told it to him because now I can refer to like the stability element and something was

missing. And then he got it, you know, like I wasn't putting pressure on him like to like be all these things. I was just telling him. But I'm really glad that I was, it's open about it cuz wow, we are friends. Yeah. And so like I was like this really interesting thing I figured out and he was interested and intrigued by it. Yeah, that's. Cool. Well, so now he, he's like, I've told him that I felt like not

good. And then he's like, OK, well, I like you and I want to change that and I want you to feel good. Wow, these are really advanced conversations. I know, and you know, that was only like date 4. So now in the future to like move forward, like he knows that like I need this thing. He's like, let's make it happen, is what he said, which is also not, I wasn't expecting that kind of reaction, you know, but like also that was a positive sign. Yeah, that's a very positive. Reaction.

Yeah to how they respond to my feedback. My grading group wreck. Damn. The OK, that's great. It's good. I'm I'm glad. Isn't that insane?

Chemistry vs. Commitment: What Really Lasts?

Yeah, like a little bit. Insane. I'm really glad that you already have an example of like how it's served you. I wasn't ready to have that example until like last. I didn't even know. Yeah, like it just happened organically. It's kind of cool. Yeah, I mean, I have another example as well of this rubric. I was dating a guy for about like four months most recently and you had to like take a second to be like computing computing. Who's she talking about? No names.

No names will be named. But I know who. It is, but she knows who it is. So jealous. I'm just kidding, but I mean, it's sister privilege. It's sister, sister, sister, sister, sister privilege. Yes, that's right, sister, client privilege. And this guy is like basically perfect in all things stability. I felt so cared for all the time like it was chocolates, flowers, dropping off chicken soup that he made when I was sick. Like this guy is like an. Angel, I was very impressed by

that. Yes, and as was I Oh my God, so thoughtful dropping me off dinner. Like I felt incredibly cared for. But I think at the end of the day, there was a lot of stability, but I didn't feel like there was enough juice between us and like the stuff that we were talking about. So in that way, like it wasn't very compatible. He's like incredibly generous and nice and thoughtful and I have nothing but good things to say about him. But I think in terms of just compatibility, like it didn't

work out for the long term. That's also kind of why the rubric started because I was just like, this guy is amazing. Like the ultimate gentleman. The like made me feel so safe all the time. I'm like, what's wrong with me? I was like, why don't I like him more? He's perfect, which is really tragic. So and I don't think you can like force chemistry obviously or like force juice. So that's actually the origin of where I got this formula from. I needed to figure it out.

I was like, what else is important to me if he's everything that I've ever asked for? She did a root cause analysis, Oh my God. Which is what we call, which is like what it's called in tech when like after you launch a product and there's some sort of issue, you kind of do like a root cause analysis to like go all the way, all the way deep and like go like all the way backwards in every single step you took to build that product and figure out like what was the cause.

Also known in therapy as a presenting problem. Because I went to my therapy. I went like I started going to therapy again and I haven't been in like 4 years. Because I was like. Therapist help. I know we've. Talked in a long time, but. I cannot figure this out on my own. And you are much smarter than me, you know, and perceptive. And so it was that like, there's nothing wrong with me, it's just that I didn't realize there are other parts of the formula that

were equally as important. Yeah, or verbalize it, I mean, yeah, you hadn't come up with a formula yet. And then also I think as a result of your most recent relationship before that you had over indexed towards stability because that was the number one thing that was missing from the previous relationship. Yes.

So that is kind of interesting. So I've learned all of my past relationships literally in my entire life have had a lot of chemistry and have been like super entertaining and fun and like, they're just like really smart people. We have a lot to talk about. Yeah. But I just didn't feel that stability element like, and maybe it's because we were never like super serious in terms of like, we're going to get married.

Like I, I feel like none of my relationships ever got to like, obviously the engagement conversation. And so maybe it didn't need that stability element. But yeah, all my relationships were very like fulfilling in the mind, but not really the heart. I don't know. Damn. You like that? Yeah, it's just funny because you didn't mean to, but you really RIP this guy. No, I'm just kidding. You said a lot of very kind things about him.

Yeah, I think OK. For me, I don't have like as structured an answer as you do. Sorry you haven't done 50 hours of therapy to dig into what the hell is wrong with. You I haven't done thousands of hours of therapy, but I still have not come up with a formula. Maybe I can think about it that way. It's an interesting exercise. I think for all of us to be like, oh, if I had to come up with a formula, what would it be?

Or like it's a good thing to react to for everyone because like seeing your formula, then that's what will make everyone else, including me, like think to be like, OK, how much do I agree with like all of your components? Which ones don't I agree with? Or it's a good? Starting point. Also feel free to disagree, I'm waiting for someone in the comments to be like ick a formula. You can't put a formula on love. Love is natural and I'm like bitch, I tried the natural way.

It's all working. Well, I mean, also I'd be very interested to know what your guys formula is. You know, like I'm, it's not like we're like experts in love and relationship, but we're happy to share all the things that we've learned and like how we've processed it and like how Cherie is approaching in the future. So anything you want to share, we're very open to hearing it.

Yes, and as you know, Jean and I read every single comment and please keep encouraging her to be vulnerable and to open up and we see all the people who are thirsting after her actually in the comments. So keep it going. OK, Thank you. Yes.

Jean's Biggest Lesson: Do Values Actually Align?

OK. So what are my learnings? I think so one, I'm coming at it from I'm seven years older than Sheree. So just by definition, I have had more experience and I've also had a very long relationship of eight years that ended last year. So I think that's also like the main differentiating factor between like our history is that I've had that like super long relationship, you know, went through everything that got

engaged. Like thought that was the person that was going to be my like forever life partner for a long like thought that for a long time, quite a long time actually. And I think like I, I don't know if this is going to come across sounding really, really, really basic, but I think my main learning from that was that it kind of all goes back to your values and what your own values

are. Understanding the values of the other person and then understanding what the combination of those two are and how that plays out in a life together. And like all of the sort of like major life milestones and circumstances you may face.

So that's kind of like the. Broad strokes of it and it's not just that it's not just like understanding your own values, but I think like really taking the the time and like annoying like effort to sort of like interrogate that and like interrogate yourself, really like interrogate yourself, interrogate that person and then like interrogate that combination and like really like hold it up to the light and like cross examination and be like. Stress.

Tested yeah, like yes, yes. Like does this really make sense? Because I think it's so easy like for me, I would consider myself to be a lover girl. Like I antic. Yeah, I'm like very romantic. Like I think it doesn't like present that way necessarily, especially on this podcast because I because this podcast is mostly about like professional stuff, but I am like deeply romantic and. I feel like I don't know that

about. You. Yeah, because like I feel like also like within our relationship, I'm more of the big sister. So like, I don't tell you everything, but you tell me everything. I'll just get up and leave now. Excuse me? Well, it's just like you haven't known me my whole life, but I've known you your whole life. Oh, just keep punching me while I'm down.

I got it. So, so, OK, So what I'm trying to get at is what am I trying to say is that I thought that like being deeply in love with someone and vice versa and also like being best friends and like building up your life together was the formula. Like I thought that that was all that it took. But I think that like having those sort of stress tests and like having those like interrogation of the values early on, as early as possible would have like really served me better.

I think a lot of it, I think it's having those conversations and also seeing it play out in actions as well. I think I am very gullible, which is why I've fallen for the juice, as they, as I say, and the chemistry in the past, you know, like I think. It's trying to make juice happen. It's juice once again. I mean, it's just, you know, when you kind of are like intoxicated and yeah, like fun and their banter and their wit, it's just like, feels like high school.

And I think I, I'm very gullible and I get pulled into that having a stability arm, like Screech. I was like, you might be a very good talker and you might be very, like, charming, but like, I need to see action behind your words. Like after we've interrogated each other on like, oh, you say this is important to you. Show me. Yeah, yeah, yeah.

The "8 Dates" Book: Why We're Intrigued...or Terrified

Is this OK if I bring up the book? Sure it's related. OK, OK, and so there's a book. So a person that I'm dating gifted me this book. It's called 8 dates and it's like 8 dates to go on or 8 date conversations to have. I've only gone on like a couple dates with this person, so getting a book is kind of. Is this him giving you his formula? Oh, maybe. But it's, but it's in the in, it's a whole book. It's a whole.

This is a lot of work. Yeah, it's a little bit like homework, but it's interesting because I, I just started reading this book and there's all these different chapters. I see there's something written on the first page. There's a message for her. Just kidding, you can't see it. It's a personal message from this person that. I can I see it later. Yeah, I'll show it to you, sister to sister. Privilege.

Sorry guys, but you know how it is like you wrote me a personal message, but these are to your point about interrogating a person. The whole philosophy about this book is that there are 8 dates, 8 conversation topics you should have and it's whether you're in a relationship now or like marry like it for all stages. Like these are things you should talk about to set, you know, ground, understanding and also

come together reignite whatever. But here are the different dates, and if things come up that you disagree with, there's like a manual of how you're supposed to talk about it actually. So the first one is how you guys think about trust and commitment. The second is how you guys address conflict. The third is on sex and intimacy. But but how are these dates? Or they're like topics to talk about on each date. Exactly. Oh my God. Yes, and the fourth is the cost

of love, work and money. How you guys think about that? Date 5 is family, date six is fun and adventure, date 7 is growth and spirituality, and date 8 is about your dreams together. And so like you're supposed to, I mean, in the beginning, in the prologue, it's just like, this is how you're supposed to have a date. It doesn't have to be an expensive dinner date or anything. It could be a walk in the park, but both be intentional and set time aside to talk about these

things. And it like literally gives you this. Is some real Stanford GSP shit here? Why I? Mean, What does that mean? It's good if you're on the same page. I could imagine if you were another person, a different person, and this person gave you this book on date or whatever number of dates you've been on, like sub five. Like, I could see someone being like, freaked out. Yeah. And like, totally making fun of this person. But Can you imagine that like some of your girlfriends being

like, he gave me a buck? Like WTF? Like he gave you this is this is like basically a couples counseling. Book it is It is a couples counseling. These are not real. They're just using the word date as like a marketing slash, like a mechanism. But this is like truly like couples counseling. This is very advanced. Unfortunately, it's worked on me. The book. I mean, I like this, the book tact. Well, the book it's. Well, 'cause I'm all, I'm all about like self growth and

learning. And I'm like, yeah. Interesting. It is interesting. It is interesting. And what it tells me is that this person is very intentional about dating you. Yeah, they're like, let's skip straight to the premarital counseling. Oh, my God, You're right. This this person is, he's interrogating straight away. You're right. Oh my God. And I didn't. Realize it. I didn't even think of that, but this is what he's doing. He's like initiating the mutual and self interrogation.

Yeah, right off the bat. Are you scared for me? No, I think you kind of like this shit. Yeah, I do. This is very, you know, touchy feely. Yes. And actually this person, which is the Stanford Graduate School of Business class that is like famous, Yeah, where people who are students, like, learn how to. Talk about interpersonal dynamics and relationships. And like, if I'm having a problem, how do I express it to you? How do I make sure that you feel

heard all this? Stuff it's their most famous class. Yes. And I think I see how it's affected you. Really. Yeah. Wait, did I ever tell you that? So one of my ex boyfriends went to Stanford GSB and he told me this was like back in like 2012 or 13. He like sent me notes from this class and was like, this class changed my life. Wow. He was like, you would love this class? Like it changed my life, full stop. Yeah. And that was why I wanted to go to GSB.

We'll see how that turned out. She was rejected from GSB but I went and she got to live vicariously through my tabs. And she was rejected from Goldman Sachs twice. She was rejected from Goldman Sachs twice. She was rejected from Stanford School of Business once. But look at her now. Look at her now. But you know what? I might go back and be a lecturer. Yeah, be a professor. Yeah, one of my good friends is now a lecturer. There, Yeah, which is so cool. She.

Teaches a class at the GSP. It'd be fun. It'd be fun to Co teach a class me and you. Whoa. Tiger Sisters takes. Yeah. Academia. That could be really fun. That could be cool. It would just be this. It would literally just be this. Just sit at the front and I'd be like, shoot the shit. Hey kids, you want to know about dating your formula, the little

rascals? Although honestly, they would be like into that, yeah, as a class, yeah, if you wanted to, I bet if you like proposed a class that included elements of like relationship and dating in long term, like they would be into that. I mean, it's funny that a lot of the classes that I've actually taken at Stanford were so based around, like, life planning. Yeah, they have many classes there. It's not even a joke. We didn't have that at all at HBS.

We have life planning, like what happens? I mean, you know, there's also a part of life planning is also like the accounting and finance part of it. There's like, oh, how do you create a trust for your family like that stuff as well? Amazing. Yeah. I wish we had that. Yeah, we we did do an exercise where we wrote a tenure letter to ourselves. That I will open in like 2 years. But this past weekend, like one of my girlfriends at in Sonoma brought up she was like, God,

this like 10 year letter. She's like, I'm just going to I know I'm just going to like RIP myself apart when I open it because, well, not in like a joking way, but she was like, it probably says like you're a billionaire who has like exited 5 companies and like you live on the shore of you know, like the, the Floribama shore with your like seven children. Like she was just kind of like starry eyed yeah, yeah And she was the other a girlfriend who is a professor at GSB now.

She was just saying, like, the main thing that she's noticed about the students is that they are so starry eyed and optimistic. And she's like, I love that. But also that's what we were like, yeah. She was like, life's going to come at you fast.

Hinge Confessions: Why Does It Feel Unhinged?

I was watching our previous dating episode in preparation for this one, and something that you said was that you were hoping to meet someone like organically, like natural in real life, and you weren't using the dating apps. How has that changed? Well. I do still hope to meet someone naturally, or I kind of just think that that's what's in the cards for me. But one of the sort of like New Year's resolutions I'd given

myself. Well, as you guys may remember, I make like every year like a list of goals that I have. And they could be like some really small goals or some are stretch goals. And it's called like the list is usually called like, you know, 35 things to do all 35 or whatever. But then I actually write like 70 things. So then if I achieve half of them, then it's 100%. Just a little bit of a little hands, just a little insight into how my mind works.

It's sick in there, but one of the ones was I was like, OK, I am going to like be on a dating app. I'm going to download a dating app, make a profile and just like be there because I think that like even if the you're even if you don't ultimately meet someone on a dating app, I think it's about like kind of like getting into the groove of dating again. And so downloaded Hinge. So that's where I've started and I just feel like it, it's like it's a mixed bag. OK, so one thing I'll say.

So first of all, I haven't been on Hinge in like 10 years and the premise has totally changed. Hinge used to be, it was called Hinge because you were connected with people who you had friends of friends in common with. That was the whole premise behind the entire app and the whole name. And like why it was useful because it was through a connection you had. Anyway, that's totally out the door. So it's like basically. Unintended. Yeah, the hinge is gone. Yes, the door, it's off the rails.

There's no, there's zero hinge. It's non hinged. It's unhinged. It's unhinged. God, that's good. That's the other name for our podcast. Well, just for the dating episodes. Yeah, true. It's basically the equivalent of like what Tinder was 10 years ago, and like everyone 10 years ago was like Tinder's, the crazy app where you could be connected with anybody. And that's what Hinge is now. It's the same thing. That's true, member. Yeah. The vibe is. Over it.

People say Tinder is for hooking up. I don't think Hinge is really for hooking up. I guess not. I don't know. But like what it feels like to me using Hinge is this is what I told my girlfriends. It's as if you were to like, walk into the middle of Times Square in New York City, stand there, and then talk to every single man or woman, but whatever your flavor crossed your path and then, like, consider them as an eligible romantic prospect.

Well, if you pay for Hinge you can also put in filters. Though the filters are not. Filtering. Filter enough. There's not enough parameters. Oh, really? Yeah. What would you add? Well, there's the friend element. There's just like. Connection. Yeah, so. I think that doesn't work in their favor 'cause then it like shrinks the people that they can show you. But I mean, it doesn't work in their favor because they want to

keep you on the app, right? But it would work in the favor of the customer because then you can have like a, a better set for of consideration. I mean like, let's be real, like the the incentives of the people that run the app. Or to keep you on the app. Yeah, they don't. They don't. Want you to find love. They say they do, but they don't want to. I'm laughing. I I'm laughing because I I as I say this my like my like old Co workers like actually run match

group and hint. Well, if you're listening, we have some feedback so. But actually that's what people say, not to bring the professional element in here, but this really famous investor named Andrew Chen from A16Z, he says he will never invest in dating apps because the model is completely messed up. Where like the outcomes of of the customers, the positive outcomes lead to less time spent on the app. So he will never invest in a dating company. Yeah, not to bring in.

The professional answer this dating episode. She had to talk about an investor. I had to talk about a 16Z. What is this threads? What is this Twitter? OK, so that's how the apps like feel like to me. But I think it's still a good and healthy exercise for me to start to do, and I'm going to just kind of like take it as it is.

LA vs. SF vs. NYC: Best City for Dating?

Yeah. Do you think you're going to look in other cities? Because I know Hinge, you can set your destination and other places. Because I think LA is a little bit tough, quite honestly. Because it is more like entertainment, like Bend to the industry, like everyone works in entertainment, talks about a certain thing, works in entertainment.

Yeah. Singer-songwriter. Well, when I went to Sonoma this weekend, I did like set the change the setting like just for shits and giggles to like pack heights and like the the app is like there's like hundreds of like hearts now. Like I can't even go through them. Like I can't. She has a, she has a backlog guys. So if you. How did Gene recently? Don't take it personally if she doesn't.

Get to you yet, It actually is. I should probably take some sort of learning from this, but like it's shocking how or maybe because I like made the parameters wider, I don't know. But it does bring to question some sort of like product market fit question? I what you mean with you? Yeah, yeah. I mean, that's. The product. Yes. No, I think I mean SF is a different type of person for sure. Yeah, I mean, just historically, San Francisco and New York City are much more professional

cities. Yeah, San Francisco, like, even by far. Because like, what else is the the city known for aside from basically like tech, Tech people who work in tech? Because in New York City there's a lot of like, artists still. There's a lot of like people who work in fashion. Well, that's professional, but yeah, I see your point. Yeah, yeah. Versus like it on top of the base, that is fine, it's true.

But in San Francisco, I think it's like the base is tech and like, I don't know what else you would say. It's like sprinkled on top of that. Also, the ratio works in the favor of women in San Francisco, whereas I've heard in New York there is way more women than men. I don't know. I just I was done fine in New York. Yeah, 15 years ago. I enjoyed New York. Yeah, 22 year old Jean enjoy New York. So should I wrap up? Yeah, yeah.

Falling for Love Again: The Thrill & The Fear

What are your your finishing thoughts? Hi. Sorry, I didn't. I didn't mean this high so dramatically. That was not planned. But I guess that's kind of how I feel where it's a mix of feeling hopeful and really excited about the future. Yeah. Because like, there's nothing like being in, I don't know, the beginning stages of what could be love. Like I think that what a beautiful time.

Yeah, that's true. Yeah. One of the things I said to my girlfriends this weekend, who is also sort of like newishly single, is that like, what is exciting is that we get to, like, go through that experience again of falling in love and like all of the, like, everything that comes with it. And it's like, I guess I never thought I was going to experience that again. And it is a really like, it's the spice of life. It's so beautiful. It's the, it's the, it's the

everything. It's like the, that feeling. It's the juice of life. Look who's the juice now? It's the, I'm trying to help her out. It's the juice of it's what makes life juicy, you know? What a fun feeling. It's not even fun. It's fun. It's just like, beautiful. It's exhilarating, the arc of like hope and like everything and like projecting forward and before the interrogation, before you interrogate, well, I. Told you guys see I this is how

you. Can this is how you know I'm a romantic because these are like the things that like I think of and I'm like excited about, but you know, balance it with some interrogation, self interrogation, mutual interrogation and then. Yes, so I feel hopeful for all of that stuff and at the same time, not to be a downer, but

Holding Hope and Hopelessness at the Same Time

like sometimes, I mean, as you can tell, like feeling a little hopeless. And I don't think that's a bad thing. Like I, I mean, of course I have the existential dread that I'm like, Oh my God, maybe I'll be single forever or like a very long time. And then that like sits with me, you know, like I, I would be lying if I said I wasn't there. But then at the end of the day, I guess I don't feel that bad. Like I think maybe deep down I'm like quite sad about that thought.

But like if I were alone for the rest of my life, like I have a lot of fun with myself. I don't. Know like I love so many different activities and things that I do. I really enjoy life. I enjoy like food and like, would it be that bad to be with myself? No, like I've already done all the work to be by myself and I love my alone time. And that doesn't mean like, I want to be alone forever, but like, and she's a really good cook.

I can survive. You would eat well yes I 40 fruits and veggies every week but. So I don't. Know it's kind of balancing both and if you guys feel similarly, please let me know because it can feel a bit lonely, but I don't know it's a mix. I think that's maybe that's what the juice of life is is like being able to hold both at the same time being hopeful and also hopeless. Oh, I thought you were saying

like having. Your, like, independence and all the things that make you you and being happy, but then also being able to, like, combine that with someone else's. It's probably both too, yeah. I think maybe that's what like life is about. It's about holding both at the same time. Yeah, what both is is up to your. Interpretation. Both of that and both of this, yeah. OK. Yeah, I just remember there's like so many other topics that we didn't get to today.

Coming Soon: Egg-Freezing & Deeper Dating Talk

We should totally do a second topic because I think that there's a lot more sort of like practical advice or like stuff that we can talk about. Like I didn't even, I meant to talk about, but I didn't even get to talking about like egg freezing. I think like that. I'm just thinking about that. I think we should do an. Entire episode on like what is egg freezing? Should you egg freeze? Should you freeze your eggs? Practical steps like biggest regrets.

Oh, it's not too late, but it's one of my biggest regrets because I don't have. Corporate funding from. Yeah, well, I've heard different advice on that, so we can tackle that next time and maybe I can let you know why you don't need to be regretful. Oh, thanks. But I won't I. Won't tell you until the next episode. Sit with that. So stay tuned, we have a lot more.

Thanks for Watching-Love You!!

To discuss and if you guys have any ideas or thoughts or comments, please leave them below and maybe we'll incorporate them into next episodes. Mailbox. Please stay tuned for the rest of season 3 of Tiger Sisters. We have some incredible interviews with our guests and Gina and I do takeaways and learnings with those episodes and we're so good sprinkling in some special episodes like this one and open to any other. Topics that you have. OK, thank you guys so much for

being here. As always, please like, comment and subscribe and rate US five stars. Leave a review. We love to hear from you guys. And until next time, bye bye.

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