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Off-the-Record: Friends Don’t Let Friends Ruin Vacation

Aug 28, 2026 · 17m

Summary

Host Rob Gunther interviews Slate writer Luke Winkley about his concept of the "parallel play vacation," where friends travel together but pursue independent activities to avoid group friction. They discuss the benefits of this low-pressure approach for adult friendships and how it eliminates the stress of coordinating itineraries. The episode concludes with a game where the hosts assign public figures like Doug Ford, Inez Cantor, and Dolly Parton to tasks such as driving to the airport, helping move, or attending an improv show.

Topics discussed

Introduction and guest Luke Winkley Defining the parallel play vacation Benefits of avoiding forced group activities Solo travel and overcoming FOMO Simplifying group vacation logistics Family vacations and potential backfires Why bachelor parties fail Game rules: Airport, Move, or Improv Playing the game with Ford, Cantor, and Parton
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