U Up?

On this week’s Sunday Special, Jared and Jordana are joined by Dr. Meg Jay, author of The Defining Decade. They start out with a discussion about how the phrase “30 is the new 20” has affected twenty-somethings’ mindsets and how gender stereotypes play into dating problems. Later, Dr. Jay explains how the “strength of weak ties” can help you meet your match. Finally, they answer an email from a li...

Jared and Jordana start this week’s episode with a conversation about Jordana’s pre-wedding feelings and prep. The first email is from a listener whose ego is bruised after a guy she thought was really into her updated his dating app profile. They’re not exclusive, and she’s still using the apps, so why does it still feel personal? The Awkward Sexual Encounter involves an unfortunate butt dial. La...

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? Lea...

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 megaphon...

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 h...

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...

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 plan...

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 listene...

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

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? F...

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

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 c...

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 relation...

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 E...

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/...

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

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...

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 wei...

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...

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, an...

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...

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...

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 e...

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...

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? Pl...