Send us a text

From awkward teenage proposals to social media engagement stunts we never agreed to, our worst proposal stories reveal the messy reality behind those picture-perfect moments everyone expects.

Nothing says romance like being proposed to at "the dystopian version of Chuck E. Cheese" on April Fool's Day, or waking up at 3 AM to a boyfriend suddenly deciding marriage will solve everything after his pastor father caught you being intimate. We share four engagement stories each, ranking them from merely uncomfortable to absolutely cringe-worthy.

The proposals range from subtle red flags (like silently slipping a ring on someone's finger while driving) to outright disturbing (a high school ex appearing sweaty and desperate in the hallway, requiring security intervention). Perhaps most shocking is the social media "engagement" one of us discovered only after friends started sending congratulatory messages about a proposal that never actually happened.

These stories highlight an important truth: bad proposals often reveal fundamental relationship issues that are easy to ignore in the moment. We explore what made us say "yes" despite the circumstances, and why these relationships ultimately didn't work out. We also discuss what we'd want in future proposals and weddings now that we've learned from past experiences.

Want to share your own bad proposal story? We'd love to hear it! Connect with us on Instagram or Facebook – we manage them separately, so you'll get different content on each platform. And don't forget to subscribe to the podcast for our upcoming episode featuring Tina from the Spokane Ketamine Clinic.

-

Support the show