We’re navigating second-guessing today! Jared tells Jordana about his latest trip to Boca, when his parents started dissecting why he’s still single, and Jordana pulls him out his own head. Afterward, they get an email from a listener concerned that her boyfriend is too much of a green flag. She spent her 20s dating toxic “boys,” so why isn’t she satisfied in a stable relationship with a mature man? The Awkward Encounter is a funny story that’ll have you clearing your Google search history. Then, a woman writes in after getting disgusted by her aunt’s reaction to meeting her boyfriend. The episode ends with a “Red Flag or Deal Breaker?” in partnership with Angry Orchard, about sharing locations, a killer dating app DM, and TikTok thirst traps.

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