On this week’s Sunday Special, Jared and Jordana break down the text messages between a listener and a guy she met through mutual friends at a wedding. After 3 dates, he sends her a text saying he’s not ready for a new relationship after his last ended, but that he’ll let her know when he’s ready to “pursue.” Is there still hope for something in the future? Or is he just letting her down easy? Learn more about your ad choices. Visit megaphone.fm/adchoices
Jul 18, 2021•27 min•Ep 258•Transcript available on Metacast On this week’s episode, Jared and Jordana are back with another Lightning Round answering 10 questions submitted by our Instagram followers all about summer dating with topics ranging from group dates to vacation communication. Plus, they discuss how to meet people off the apps and whether or not serious relationships are possible during IRL Summer. Learn more about your ad choices. Visit megaphone.fm/adchoices
Jul 14, 2021•1 hr 23 min•Ep 257•Transcript available on Metacast Jared and Jordana are back with another Deal Reveal on this week’s Sunday Special. A listener shared screenshots of her conversation with a guy she was seeing long-distance for about two months. It was supposed to be casual, but she caught feelings and his reaction was confusing. If he says he didn’t want to end things, why would he still be using Tinder? Can she still bring this up even if they haven’t put a label on it? Plus, they discuss what it actually means to use someone. Learn more about...
Jul 11, 2021•23 min•Ep 256•Transcript available on Metacast On this week’s episode, J&J start out with a recap of Jordana’s bachelorette party. The first emailer asks how she should respond to her friends’ concerns about a guy she’s seeing. Why won’t they elaborate on their warnings? And should she give him a chance to explain himself? A listener’s fiancé confesses a dirty little secret during the Awkward Sexual Encounter. Then, a listener asks if you can get back together if the breakup was for mental health reasons. Should he reach out or let it go? La...
Jul 07, 2021•1 hr 28 min•Ep 255•Transcript available on Metacast On this week’s Sunday Special, Jared and Jordana are joined by psychotherapist and author Lori Gottlieb. They start out with a discussion of what type of relationship issues Lori sees in therapy and how COVID has impacted them. Then they get into Lori’s book Marry Him and what you should actually look for in a long-term partner. Later, they answer an email from a listener who is anxious about planning a future with her boyfriend. Is it normal for her to feel she should date around more? How can ...
Jul 04, 2021•36 min•Ep 254•Transcript available on Metacast On this week’s episode, Jordana and Jared start out with a tale about Jordana’s phone and her plans for her bachelorette party. Then they answer an email from a listener asking if a f*ckboy can change his ways. Does him not wanting to hook up mean he’s more into her or less? The Awkward Sexual Encounter almost ended with penis surgery. Then (content warning) at around the 49 minute mark, a listener shares a story about being harassed by a stranger and asks how to turn down men when they hit on y...
Jun 30, 2021•1 hr 24 min•Ep 253•Transcript available on Metacast On this week’s Sunday Special, Jared and Jordana are breaking down the texts between a listener and a guy she ended things with after six weeks because he never wanted to sleep over. Did she end it too soon? Or did she never really like him in the first place? Plus they discuss miscommunication when it comes to dating expectations. Learn more about your ad choices. Visit megaphone.fm/adchoices
Jun 27, 2021•28 min•Ep 252•Transcript available on Metacast On this week’s episode, J&J start with an email from a listener asking how to keep the dating momentum going while you’re traveling. Should she try to keep in contact while she’s out of town? The Awkward Sexual Encounter is a dinner disaster. Later, a listener asks how to deal with being stereotyped by people she’s dating. Are stereotypes the real reason this guy doesn’t want to take her hiking? Finally, Jared and Jordana are joined by Jared’s college ex and author Ashley Bisman for a round of R...
Jun 23, 2021•1 hr 17 min•Ep 251•Transcript available on Metacast On this week’s Sunday Special, J&J answer an email from a listener about how to deal with breadcrumbing. Should you call the breadcrumber out? Are you also a breadcrumber for continuing the conversation? Plus they discuss how to take control of your dating life. Learn more about your ad choices. Visit megaphone.fm/adchoices
Jun 20, 2021•22 min•Ep 250•Transcript available on Metacast On this week’s episode, Jared and Jordana start out with a discussion about freezing your eggs and what it means for dating. Then they answer a listener's email about sliding into someone’s Twitter DMs. Can Twitter DMs be used for dating like Instagram? What should she say to make her move? An emailer finds a surprise in her sink during the Awkward Sexual Encounter. Later, a listener asks how to compromise on decor when moving in with your significant other. What can differences in decor style t...
Jun 16, 2021•1 hr 21 min•Ep 249•Transcript available on Metacast On this week’s Sunday Special, Jared and Jordana are joined by relationship and sex columnist Dan Savage. They start out with a discussion of how Dan’s advice has evolved over the past 30 years and his thoughts on monogamy. Later, they answer an email from a listener whose ex-boyfriend left her for the same woman they had a threesome with. How should she approach threesomes in her current relationship? Plus, they discuss how to develop trust and boundaries in an open relationship. Learn more abo...
Jun 13, 2021•56 min•Ep 248•Transcript available on Metacast Jared and Jordana start this week’s episode with a conversation about the world opening back up when you’re single versus when you’re in a relationship. Then they read a break up contract sent to a listener by her now ex-boyfriend. Can you take a long-term relationship back to a short-term relationship? How do finances play into a breakup? A listener learns about blue balls in the Awkward Sexual Encounter. Later, J&J answer an email asking exactly how to have a hot girl summer. Finally, Dylan Ha...
Jun 09, 2021•1 hr 21 min•Ep 247•Transcript available on Metacast Jared and Jordana are back with another Deal Reveal on this week’s Sunday Special. This week’s emailer wants to know if her ex actually wants to be friends or if there’s another reason for him staying in touch. Is it ever a good idea to stay friends with an ex? J&J break down why he’s holding onto the friendship and what she should do about it. Learn more about your ad choices. Visit megaphone.fm/adchoices
Jun 06, 2021•25 min•Ep 246•Transcript available on Metacast On this week’s episode Jared and Jordana are back with another Lightning Round, answering 20 questions submitted by our Instagram followers with topics ranging from first date conversations to spicing up long-distance relationships. Plus, they discuss the best pictures to use on dating apps and how to correct someone’s kissing style. Learn more about your ad choices. Visit megaphone.fm/adchoices
Jun 02, 2021•2 hr 48 min•Ep 245•Transcript available on Metacast J&J are back with another Sunday Special all about personality types and how they factor into dating. They answer an email from a Type A listener with a Type B boyfriend who doesn’t know how to deal with their differences. Do these personality types actually determine compatibility? Do opposites attract or are their differences in cleanliness and punctuality a deal breaker? Plus, they discuss how to assess which qualities are most important to you in a partner. Learn more about your ad choices. ...
May 30, 2021•20 min•Ep 244•Transcript available on Metacast On this week’s episode, Jared and Jordana start out with a pep talk for going back out into the world. Then they answer an email from a listener who doesn’t know if she should ask someone out at their workplace. Is there an appropriate way to show someone you’re interested without making them uncomfortable? A listener gets an unpleasant surprise during the Awkward Sexual Encounter. Later, they weigh in on an email from a listener wondering what it means for her relationship that she actually enj...
May 26, 2021•1 hr 14 min•Ep 243•Transcript available on Metacast Jordana and Jared are back with another Sunday Special, and this week they’re reading texts from a listener who thinks she might have ruined her chances with a dating app match by drunk texting him. The emailer describes her previous pattern of drinking too much and scaring guys off with her drunk texts, but she got it together during quarantine and finally feels ready to get back out there. That is until a night out with her coworkers. How should she address the drunk texts? And should she tell...
May 23, 2021•31 min•Ep 242•Transcript available on Metacast J&J start the show with a conversation about Jared’s relationship status. The Awkward Sexual Encounter involves a 69 gone wrong. Later, they answer a listener email about a guy who wants to be in a one-sided open relationship. Is it a red flag that he wants her to sleep with other people? Jared and Jordana finish the episode with a round of Red Flag or Deal Breaker about vaping, voice messages, and airport hygiene. Learn more about your ad choices. Visit megaphone.fm/adchoices
May 19, 2021•2 hr 36 min•Ep 241•Transcript available on Metacast On this week’s Sunday Special, Jared and Jordana are joined by Tinx, and they start with a discussion about the differences between dating in NYC, LA, and San Francisco. Then they dive into Tinx’s dating life and her Box Theory about the right time to sleep with someone you’re dating. Later, they answer a listener’s email asking if she should tell her best friend she has feelings for him, and Tinx shares her personal experience of falling in love with her best guy friend. Learn more about your a...
May 16, 2021•55 min•Ep 240•Transcript available on Metacast Jared and Jordana are back with another episode, and they start out with a discussion of the viral video of Ben Affleck shooting his shot with a woman who unmatched him on Raya. The first email asks how to deal with going back to the office when her boyfriend wants to continue their nomadic pandemic lifestyle. The Awkward Sexual Encounter involves three condoms and a dog. Later, J&J try to figure out why a guy bailed on a listener in the middle of their first date. They finish the episode with a...
May 12, 2021•1 hr 6 min•Ep 239•Transcript available on Metacast On this week’s Sunday Special episode, Jared and Jordana are joined by Matchmaker Maria. They start out with a discussion about how Maria got into matchmaking and how she applied her matchmaking strategies to meeting her own husband. Maria breaks down how the matchmaking process works, the types of guys who hire matchmakers, and how men and women differ when it comes to matchmaking. Later, Maria explains when to have sex with someone new using her 12 date rule, and they answer an email asking ab...
May 09, 2021•58 min•Ep 238•Transcript available on Metacast This week, Jared and Jordana start out with a discussion about experimenting with your look. The first email asks about the etiquette of orgasms. Is it ever okay to fake it? The Awkward Sexual Encounter is almost too gross to believe. Later, an emailer asks J&J to sort out her boyfriend’s shady phone behavior. Is it always a bad sign if your S.O. doesn’t want to share their passcode? Finally, they finish the episode with a round of Red Flag or Deal Breaker that sparks a discussion about someone’...
May 05, 2021•1 hr 13 min•Ep 237•Transcript available on Metacast Jared and Jordana are back with another Sunday Special, and this week they’re breaking down texts from a “verbose fuckboy.” The listener received some very lengthy text messages from someone she was dating essentially saying, “it’s not you, it’s me.” Does his long explanation and apology mean he is being genuine? Or is he just like other guys who run at the first sign of a serious relationship? Plus, they discuss what actually makes someone a f*ckboy. Learn more about your ad choices. Visit mega...
May 02, 2021•30 min•Ep 236•Transcript available on Metacast On this week’s episode, Jared and Jordana start out with a conversation about the energy in NYC and the post-pandemic dating scene. The first email asks how to have casual relationships without feeling disrespected. Are they always just about 2AM booty calls? The Awkward Sexual Encounter involves a bed wetter and an early morning streak across a college campus. Later, a listener writes in hypothesizing that you shouldn’t date someone who’s new to your city if you’re looking for a serious relatio...
Apr 28, 2021•1 hr 21 min•Ep 235•Transcript available on Metacast Jared and Jordana are back with another Sunday Special, and this week they’re talking all about relationships with coworkers. An emailer writes in wanting to know if her work crush is flirting with her or just being friendly after their first Zoom meeting felt more like a first date and he offered to help her move. Should she make another move after her initial ask for drinks fell through? Plus, they share their general advice for navigating romantic relationships at work. Learn more about your ...
Apr 25, 2021•37 min•Ep 234•Transcript available on Metacast On this week’s episode, Jared and Jordana start out with a conversation about the paid bonus features on dating apps and if using them makes you look desperate. Would you be turned off by someone sending you a Hinge rose? This week’s Awkward Sexual Encounter is surprisingly nutritious. Later, an emailer writes in asking how to find an “ass-smacking nice guy” after not feeling the sexual chemistry on first dates. Is there a middle ground between the guy who’s too shy to make a move and the guy on...
Apr 21, 2021•1 hr 17 min•Ep 233•Transcript available on Metacast Jordana and Jared are back with another Sunday Special, and this week they’re dissecting texts between a listener and a guy who keeps rescheduling their dates. The emailer thinks the chemistry is there but worries he’s only looking to hook up. How many chances should you give someone to schedule a real date? Should she give him another chance if he reaches out again? Plus, they discuss how to know if a guy is taking you seriously. Learn more about your ad choices. Visit megaphone.fm/adchoices
Apr 18, 2021•30 min•Ep 232•Transcript available on Metacast On this week’s episode, Jared and Jordana start out with a discussion about adult braces and sharing your space with a significant other during quarantine. An emailer sends in a screenshot of a dating app conversation where she sets her standards of looking for a relationship, but she isn’t sure if the response is sincere. At what point does the “what are you looking for?” conversation actually matter? During the Awkward Sexual Encounter, a listener gets nostalgic about a water bed mishap. Later...
Apr 14, 2021•1 hr 6 min•Ep 231•Transcript available on Metacast Jordana and Jared are back with another Sunday Special, and this week they’re discussing when you can assume exclusivity with someone you’re seeing. A listener writes in after her DTR conversation with a long-distance romance did not go as she hoped. Was she reading the signs all wrong? Plus, they talk about the clues that someone is a lazy dater. Learn more about your ad choices. Visit megaphone.fm/adchoices
Apr 11, 2021•27 min•Ep 230•Transcript available on Metacast On this week’s episode, Jared and Jordana change things up with a lightning round of questions submitted by our Instagram followers. Instead of our usual email format, they answer 20 questions with topics ranging from how to get excited about using the dating apps, to running into exes, to how to get your S.O. to go to therapy. Plus, they give their best tips for moving in with your partner, making a dating app profile, and reaching out to a fling that ended because of the pandemic. Learn more a...
Apr 07, 2021•1 hr 14 min•Ep 229•Transcript available on Metacast 
