Dear Treehouse #22 | Valentine’s Day Stories: Best, Worst & Dating Disasters

The Treehouse Show Podcast · May 4, 2026 · 22m · transcript

Valentine’s Day brings out the best—and the absolute worst—in dating and relationships. In this episode of The Treehouse Show, we share our best Valentine’s Day memories, the worst dating fails, and Trey tells a heartbreak story that sets a new standard for bad Valentine’s experiences. If you enjoy comedy podcasts about relationships, dating stories, and real-life humor, this episode delivers. Topics include:

Best Valentine’s Day moments

Worst Valentine’s Day disasters

Funny dating and relationship stories

A brutal heartbreak story you won’t forget

About the show:

Leave your worries outside…