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

September 16, 2026

AI Summary

5 min read

A Groomsman's Wife Skipped the Wedding, and a Boyfriend Demands 25 5Ks Before the Ring

In this episode of U Up?, hosts Jordana Abraham and Jared Freid field listener emails about relationship dynamics, boundary-setting, and what happens when partners stop optimizing for "we" and start acting like individuals. The throughline is about calibrating expectations in long-term relationships — when to compromise, when to walk away, and how to read whether someone is genuinely negotiating or just looking for an exit.

The TSA Pre-Check Question: Waiting as a Relationship Currency

A listener described overhearing a couple in their 50s at airport security. The husband said he would have left his wife behind in the regular line without a second thought if she didn't have TSA PreCheck. The listener's boyfriend had waited with her before she got PreCheck, and she wondered: is this normal after 25 years, or a red flag?

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What you'll learn

  • 1 Timestamped Outline
  • 2 (00:00) **Opening Banter & Hilton Sponsorship** - Hilton ad and intro to the show
  • 3 (01:07) **Jordana's Montauk Trip & Dog Drama** - Jordana recounts a chaotic family vacation and a boarding disaster with her dog Ronnie
  • 4 (14:49) **Yankee Game & Baby Update** - Jordana describes taking her twins to a luxury box at Yankee Stadium
  • 5 (17:58) **Peaks and Pits of the Trip** - Jordana shares the best and worst moments of the family vacation
  • 6 (20:19) **Mika Frozen Yogurt Review** - Jordana and Jared debate whether the trendy Greek frozen yogurt spot is just rebranded Pinkberry
  • 7 (27:41) **Jared's Netflix Special & Press Tour** - Jared reflects on the emotional rollercoaster of releasing his comedy special and doing press across the political spectrum

+ Full timestamped outline available in the app

Guests on this episode

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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