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J&J are tackling nuance in the modern dating world. Before jumping in, Jordana recounts her Sonoma vacation and her driverless ride reminds Jared of dating apps’ impact on society. Plus Jared has feedback for a fan that shot her shot for an upcoming tour date, and his reasons for what was wrong with her approach tie into the first email. A listener has a crush on her fitness instructor, but is there a way to shoot her shot without making it awkward if he wants to pass? In true U Up? fashion, John Mayer enters the tangent fray, but first, J&J have an introduction to make. Then, the Awkward Encounter involves a situation going from flirty online to uncomfortable irl when a listener finally meets her colleague at graduation. Next, J&J answer an “Are We Dating?” about a long-distance connection growing between traveling work trips. The episode ends with a “Red Flag or Deal Breaker?” about seatbelts, professional Tinder pics, and IG explore pages.

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