U Up‪?‬ U Up?

Before diving into emails, J&J get caught up in the sitcoms of the 90s. Plus, they follow up on a recent "Petty or Prudent?" after a YouTube comment schools them on the difference between kinks and fetishes. Then, the first email comes from a listener concerned her guy friend’s intentions may be more flirty than friendly. The Awkward Encounter will make you think twice about where you hide your sex toys. Next, a listener is her boyfriend’s first girlfriend and that’s been noticeable as their relationship continues, but how much onus is on her to help him mature? The episode ends with a “Red Flag or Deal Breaker?” about whether kissing gay friends counts as cheating, a traveling quirk, and a lack of boundaries with coworkers.
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This Sunday Special is a dream brunch group as J&J are joined by Keltie Knight, Becca Tobin and Jac Vanek of The LadyGang podcast. They start with learning the famous toxic ex origin story behind The LadyGang’s formation before J&J get into relationship icebreakers and questions that will tell you exactly how everyone’s relationship style differs. Then, they play a round of Firsts and Worsts, for a lightning round catchup on The LadyGang’s past and present relationships. Plus, Jared is outnumbered being the only one both single and male in the chat. Keltie, Becca and Jac each share differing marriage dynamics and perspectives on their past, and Jordana relates to one more than anyone else. The episode ends with a “Petty or Prudent?” about a male listener on the brink, wondering whether he should skip being his girlfriend’s wedding date to avoid being part of her family’s memories if a breakup will happen any day now.
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Long intro lovers, today is your day! J&J have a lot to unload this week, from the one quality Jordana’s husband isn’t in love with to Jared’s weekend in the Hamptons with Hannah Berner, and a one-and-done take on this season of Love Island USA and that Casa Amor shakeup. Next, J&J get an email from a listener four years into her relationship and itching to know whether I do’s will ever be in their future. The Awkward Encounter is a trip down memory lane. Then, a male listener writes in wondering how his female coworker is getting so much attention on Hinge (no offense). The episode ends with a “Red Flag or Deal Breaker?” about changing dating app photos, misused prompts, and an uncomfortable date.
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J&J are treating Benefits listeners to a different kind of existential crisis as Jared recaps a coffee shop run-in from a few hours before they got to the studio. To set the scene, he’s sporting his signature “Ass Man” cap (a Seinfeld reference if you missed that show or any explanation he’s already given) and stopped by his go-to West Village, Blackstone. Someone approached him questioning the cap, but while they felt like a stranger to him, he was clearly familiar to them. His discomfort with the lack of recognizability on his end takes him back to a random text he got on the road. Jordana reminds him that to fans, Jared is on a pedestal, but from his perspective, he’s at a disadvantage when he tries to have genuine interactions. She helps coax him out of a fear of causing disillusionment to people he meets.

We’re deep into summer and Jared’s in a bit of a rut. He talks Jordana through where his mind’s been while he’s been on the road. Then, they kick off the Sunday Special with a round of “Icky or Picky?” about a secret kink. Our listener stumbled upon her date’s Reddit and saw his activity in fetish communities online and, after witnessing what he was into, she felt turned off. Next, J&J answer an email seeking redemption for revenge. Our listener is happily married, but still pining over the perfect way to tell her ex off. Jared and Jordana speak about the attempt at winning in relationships and seeing beyond the traumas of the past.
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Double-standard debates in the dating world are weighing on us today, specifically those that are more of an issue for women than men. Before diving into emails, Jared and Jordana discuss the backlash to a Forbes article, “Are We Still Not Ready For A Mixed-Weight Romance On Screen?”, and the topic of mixed-weight relationships in general. Next, the first emailer wants to know how to let a guy know that you aren’t interested in hanging out when you still have to work – or be stuck in some capacity – with him. The Awkward Encounter is a dating don’t when you’re feeling anxious. Then, the second emailer needs help navigating her way out of a sticky situationship. The episode ends with a “Red Flag or Deal Breaker?” about prolonging the talking stage, living with an ex, and leaving out an important detail post-sex.
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