Finding Our Perfect Match

It's hard to write a good profile because you have to really examine these tiny nuances like you don't have much space, but that means you have to have a really tight message, like who am I from the perspective of someone that I would want to like me.

Welcome back to On the Job Today, we're speaking with Grace Lee, a professional dating coach based in New York City.

My business is called a Good First Date, and we started in twenty eighteen, and I work with men and women of all ages and situations on every aspect of dating, with my primary focus being online dating, how to optimize that your dating apps and everything that comes after that.

Now, before you go thinking we've changed the format over here and On the Job, Grace and I are talking about much more than just dating on today's episode. Beyond learning what it means to be a professional dating coach, we'll uncover the surprising similarities between our romantic and professional lives. So even if you're happily hitched or dead set on staying single, stick around to get some valuable advice from this dating pro Being a dating coach was not something Grace Lee set out to do.

I actually started working in corporate banking, and then when my daughter turned one, I left the bank completely. I opened a boutique in Shanghai, and then I sold children's things. It was really that great thing that happens when you are obsessed and love something and then suddenly it's your job and you get to do it all the time.

On paper, everything was going well for Grace. She had a diploma from a good school, a successful career, a husband, kids, all the pillars of a thriving life. But in two thousand, in a nine, Grace's life took an unexpected turn with a divorce and a move to New York City. And that transition period was as challenging as you'd imagine.

I got married when I was twenty six, and before then was pretty much a serial monogamous, so I had never really dated. And since I got married kind of young, I'd never had that experience of just being single and living that single person's life.

But now there she was, thrust into a big, new city and this unfamiliar phase of life.

I remember the first date I went on after I got separated. Couldn't believe how intense it was emotionally. It was like the whole, like the whole box of crayons, like every single emotion, from being completely obsessed and fixated to feeling like totally tragic, like nothing ever good will ever happen to me again.

In time, though, the intensity of those emotions settled down and Grace started doing enjoy the process of going on dates. They offered her a healthy relief from the shakeup of the divorce and then responsibilities of single parenting.

So when I moved to New York City, I had two little kids and mash dot com was just starting to get fired up, so I took the opportunity, was really curious and leaned heavily on match and just started dating a ton.

Dates were also a great way for Grace to explore her new hometown and engage with people she'd never have met in the finance world.

Being a parent, like having little kids, and also I was working in banking at the time, so that was my circle. And then suddenly with online dating, I could match someone from a completely different world, and I loved I loved the experience of just sitting down with someone and imagining myself in their childhood and what they did. It's kind of how also how I discovered different parts of the city, and it just really opened my mind to life outside of being a banker and having little.

Kids were once the idea of having to go out into the dating world seemed overwhelming and intimidating. Soon Grace couldn't wait for her next date.

I think because I was fresh out of a divorce and I didn't have any experience. I really went in full force and dated many, many people. You know, I was one of these people that might have gone on three or four dates a week.

And being the organized professional type, Grace even made a spreadsheet to keep track of her potential suitors. Do you remember what some of those columns might have looked like?

Sure, I mean there were basic ones, you know, age, I profession, something about it was fun to talk to them, might have been like a personality score, what they did for work, how much money they had, what neighborhood they lived in. I'm not proud to admit that, but that was definitely on the spreadsheet, just like it is in a database for any matchmaking service. And there's probably an attractiveness rating that fell outside of age and height, just if I was attracting them or not.

And while Grace was doing fine on match dot com, She also put her name on one of those professional matchmaking databases and shortly thereafter gets invited in to fill out a questionnaire.

They were asking me all kinds of questions and doing it in a very serious way, like why are you still single? What are you looking for? It was on your red flag list? All of these questions that are actually so fun to answer, and all of this information is there to help them match people well.

And Grace found this whole process fascinating.

So I remember during that interview looking at her and asking her if this was a real job, because I couldn't believe that this was someone's profession. And long story short, I was never match with that client, but I ended up working as a matchmaker.

And initially Grace loved matchmaking, especially compared to banking.

Speaking about the differences between matchmaking and working in Kaindance. The Monday morning meeting for matchmaking is hilarious. It's a bunch of matchmakers talking about their clients, talking about people in the database. Do you think that this person would go all with this person? So it was like getting paid to gossip, but of course in a very professional, purposeful way.

But while Grace really enjoyed meeting her clients and helping them in their romantic journey. She found the particulars of matchmaking less than ideal. Well, not to mention, from her own dating experience, she knew that the dating apps, which were really gaining in popularity at this time, did a pretty good job of connecting people. That is, if you knew how to make an effective profile.

I realized, like, I can help people get on a good first I'm very, very good at getting people on a good first date.

So that's when Grace pivoted from being a professional matchmaker to a professional dating coach.

There's a lot of work that goes into helping clients come up with their profile. It's intensely creative personal work. So it's really a matter of figuring out how to help people make their profile more like them, to be a better representation of them, and then also to teach them how to swipe and text so that they can filter people out and go on the days that they want to go on.

To do this, Grace meets with her clients one on one and tries to get to the core of who they are.

I'm always scanning for those things that are going to make them stand out because they're in a pile of thousands of people and they have a moment to make an impression, and then how do you present that. It's tricky.

And while it might be tricky to boil someone down to a limited amount of text and a few pictures, when it does happen, Grace will tell you it feels better than banking. Ever. Did I love it?

When we come out on the other end and we have it. When we nail the thing, it's like, Oh, feels so good, like we got it. Then the person forget the date, they're looking at the profile and they're like, Wow, I'm actually a pretty interesting person.

In this way, Grace is helping people take stock of their lives to highlight what makes them unique, capturing their personality, and celebrating their achievements, and then to present all that to the world with the hope of catching someone's attention, which sounds pretty similar to sending out resumes and cover letters,

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We're back with professional dating coach Grace Lee. Through her service A Good First Date, Grace helps people put their best foot forward on dating apps and other online dating platforms. But it's not just our love lives that have gone digital. Job applications are submitted online, meetings happen over zoom, and most of our work communication these days runs through email

I think in a CV it's a little bit less esoteric. There is more standard ways of presenting yourself, so it's like kind of have to figure out those key things about yourself, how do you want to talk about them? And if you can take your ego out of it, you can start to think more carefully about how you're presenting yourself.

As you all learned in a previous episode this season, a lot of our online job applications are first reviewed by AI, so yes, you need to have all the pertinent information in there, but eventually, hopefully your CV will reach human eyes. And just like with a dating profile, you want your CV and cover letter to catch that person's attention with clear and gauging messaging.

So just thinking about, Okay, the other person is sitting there with your CV, they have a checklist of things that they're trying to tick off to move you to the next round. They're not invested in whether or not you get.

The job or not.

They kind of want you to because they don't want to keep doing this thing. They just want to find the person already.

And while it might be tempting to make one resume and send it out to every job, Grace recommends customizing your messaging to the job you're seeking.

In that case, it's going to be about highlighting what was interesting about your job. So if you're going into the hospitality industry, that job that you had over the summer serving coffee is actually going to be more relevant than your private equity job.

And this isn't a send it and forget it sort of thing either. Just as Grace made a spreadsheet to keep track of our dates, as job applicants, we need to reflect on the responses our applications get. We need to ask ourselves what's working, what isn't, and then fine tune our messaging based on that feedback.

Yeah, it's like I can't believe I didn't get invited to any first round interviews for banking. I can't believe it, and then just being curious about it, like, oh, I wonder why not. Maybe there's a good reason.

Eventually, though, if you get through those early rounds, you'll be asked in for an interview, and Grace says interviews bear an uncanny resemblance to a first date, despite the formalities. It's just two people trying to get to know one another.

So for every single thing you have on your CV, have a story, and that story should be about how what you did makes you qualify for this job, and that story should just be interesting and fun, one that you enjoy telling, so that you have a good conversation.

So in the same way you might highlight your love of live music on your dating profile. Grace suggests coming into the interview with a strategy to move the conversation in a purposeful direction.

Let's say you're going to an interview and you really want to learn about AI. That's something that you want to do in your career. So you want the conversation on the interview to touch AI at some point, and you want it to be pretty central, so that you can talk about the things that you've done on your own and you can analogize how those skills might help a company like theirs. Even if the job that they're trying to interview you for may not be an exact fit.

And we should also remember that the interview is a two way street.

You can show them that you're interested in a lot of ways by being attentive by being interested in their story, by sharing things about yourself that you want them to know, and then you have to let them meet you half way too. I would try to touch on a lot of different topic until I found the one that I thought they were comfortable with. Then they can bring themselves out and that's when you can test real compatibility.

That same advice still applies after you get the job, or even if you've had the same job for decades, because at the end of the day, no matter what we do for work or how long we've been doing it, our professional lives revolve around interpersonal relationships. As Warren Buffett said, partnership is not a legal contract between two equal individuals. It's an emotional alliance between two people who are committed to each other's success.

The number one thing you need in any situation, job, romance, friendships is mutual interest. And when we don't have that, things like point fall apart.

And speaking of falling apart, since we're talking about relationships of all sorts here, it'd be wrong not to acknowledge that sometimes they break down, that our passions wane, or a job just run its course. That isn't to say we should all be quick to jump ship and run to the next new thing. Lasting rewarding relationships take work and commitment, but if that time comes grace. Lee has learned from personal experience that sometimes starting a new is just what we need.

I love getting to know my clients, and I love watching them have these breakthrough moments where they come to me and they're so worried about something, and those moments where I can just reassure them that they're doing fine. Yeah. I want people to feel good about their lives and optimistic about what could happen, and confident that they're doing everything they can to find the person they want to be with.

For on the job, I'm Avery Thompson