How Do I Turn My Work Hookup Into A Real Relationship?

J & J start the show with a conversation about Jared’s birthday and the difference between how men and women celebrate. Then an emailer writes in to ask why the guy she is seeing insists on using a condom every time they have sex even though they’re exclusive and she has an IUD. Is this a sign that he’s hiding something, or is he just overly cautious? The Awkward Sexual Encounter of the week features a night of shots and an ugly-cry. Why are guys judged more harshly for showing emotion in a relationship? Next, a listener asks why her office-party hookup hasn’t asked her on a date yet, and whether or not they’re ever going to go out. Another emailer asks whether or not it’s fair to judge a guy she matched with on a dating app who was going bald but didn’t disclose it until the first date. They close out the show with a game of Red Flag or Deal Breaker featuring the age old question: what do you do when your boyfriend accidentally calls you mom?

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