What’s An Appropriate Age Gap?

Jared and Jordana are diving into listener emails, and one is about an ex who still wants to join a football betting pool even after a breakup over Bad Bunny the day before an important abortion appointment. Another emailer asks J&J how to get out of a 14-year situationship with ...  Show more

Jordana and Jared learn that Tobey Maguire officiated his ex-wife’s wedding just weeks after finalizing their divorce, and they debate whether it’s sweet or just super weird. They then help a newly married listener who can’t fall asleep without listening to a podcast while her hu ...  Show more

Age gaps are on tap this week and we're discussing it all — dating older, dating younger, pros and cons, power imbalances, sexual compatibility, and more. We share our (and our listeners') experiences of dating with an age gap and what to look out for if you venture into this typ ...  Show more

How big is TOO big of an age gap in dating?? Dean reveals what happened when he dated an older woman when he was in his early twenties!   Sharing your location with your significant other can be a sensitive subject in a relationship, and we hear about how Dean got caught by Caely ...  Show more

In this week’s episode, Shantal, Lynnie, and Gary answer even more fan-submitted questions—from what makes a hookup truly unforgettable to how many “okay” dates is too many before moving on. They are talking sex confidence vs. physical skill, the surprising impact of rejection, a ...  Show more