Why won’t Jared go to therapy? We get this question often and, this week, he shares his own thought on why as well as a helpful TikTok, "Men Who Wear Masks And Struggle With Conflict" by @elisemicheals. Plus, he and Jordana are slipping more into f*ck it mode for the holidays. The first email is advice ahead of office holiday party season when your coworkers ... Show More
Apr 24
Should You DM the Girlfriend If You’re the Other Woman?
Jordana and Jared kick things off discussing their night before at a fun client dinner that somehow turns into a lesson about the one airplane seat that always survives a crash (allegedly, 11A)! From there, they get into travel drama, including middle seat horror stories, whether ... Show More
46m 2s
Apr 22
He Matched With Me… And My Brother! A Dating App Nightmare
Jordana and Jared are back in the studio and immediately spiraling about NYC heat, aging, and why early flights now require a full recovery day! They debate whether a man in his late 30s sleeping in a twin bed is an instant ick and why his mom might be the bigger red flag. Then, ... Show More
56m 42s
Apr 2025
Awkward Tuesday: In Greg We Trust
Our listeners love dysfunctional relationships so much, we didn't wanna deprive you. Here's a segment from our Full Show feed, 'Brooke and Jeffrey', that may have even more drama than a Second Date Update. Let us know what you think! What happens when you go on 3 dates and one ... Show More
16m 20s
Aug 2025
Sophie & Chris - When Your First Date Knows Your Ex… and His Friends
Sophie thought she’d found unexpected chemistry with a guy she’d known for years — her ex’s best friend. But after one amazing night, he vanished. Now she’s on the hunt for answers, and what comes out involves surprising friend group drama, rumors, and a revelation neither of the ... Show More
12m 15s
Feb 2025
Office Hours Amy Nobile Messing Takes Us Deep into Dating
<p>This week holistic dating coach, Amy Nobile Messing takes us on a guided tour of all the good and bad of dating. We get some hard truths about chemistry, second dates, and what to shut about early on in the process. Then in a moment of vulnerability I open up my phone and ha ... Show More
51m 50s