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My Boyfriend Won’t Propose Until I Run 125 km!

September 16, 2026 · 1 h 37 min

Show notes

Jordana tells Jared how her vacation ended up being the busiest and most unrelaxing, but also the most fun, due to Ronnie the dog getting kicked out of boarding for peeing and joining the family’s chaotic Montauk trip! They then get into listener emails and discuss whether a partner should wait in the regular TSA line, what actually marks the end of the honeymoon phase, and whether small gestures like Trader Joe’s flowers matter more than big romantic moves. They also talk about a passionate “lake life” man who may have used his love of camping as an excuse to break up, and whether a fantasy football draft on your wife’s birthday is a red flag or deal breaker. We say yes!

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