Episode 45: 50 First Dates kicks off with a very important update: Shawn’s hair. After shaving his head since his twenties, he finally let it grow out. The results land somewhere between Captain Picard and a clown, and yes, that comparison sets the tone for what follows.

From there, we move into the heart of this Valentine’s Day special. A few years ago, Leah gifted Shawn The Adventure Challenge: Couples Edition, a book packed with creative date ideas. One challenge asks you to uncover a memorable date from your parents’ past. That leads us to a recorded phone call between Shawn and his dad, who shares some surprisingly cool and thoughtful date stories from his younger years.

Naturally, that sparks a bigger conversation. We reflect on our own memorable dates, including first dates, misfires, and moments where reality didn’t quite live up to the fantasy. Some dates felt magical, others felt awkward, and all of them taught us something. Along the way, we talk honestly about expectations, effort, and why no relationship follows a perfect script.

Next, we dig into the history and meaning of Valentine’s Day itself. We explore where it came from, how it evolved, and why it still manages to stir up so many feelings—both good and bad.

Then, the conversation takes a practical turn as we chat about our Etsy shops. Sales, views, and visits are all down, which leads us to wonder out loud: did Etsy change the algorithm again, or is something else going on?

Finally, we wrap things up with future plans and daydreams. An anniversary road trip in May is on the table. Shawn might hit the road to Toronto in June with his brothers for a Godsmack concert. Plus, he reveals his newest obsession: buying a metal detector… even though he has no idea which one to get.

This week’s podcast promo: The Flopcast

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