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

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

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 momentsWorst Valentine’s Day disastersFunny dating and relationship storiesA brutal heartbreak story you won’t forgetAbout the show:Leave your worries outside and…