As winter weather blankets the Billified studio, Bill dips into the archives to bring you heartwarming (and sometimes heartbreaking) moments from the first 100 episodes of this now 550+ episode journey. In this Valentine's weekend special, we're revisiting some unforgettable stories of love, loss, and everything in between.

Travel back to Episode 5 for the notorious tale of Bill's awkward encounter with Dan's first wife on her date with another man – a story that would become Billified legend. We'll then revisit Episode 20's sobering discussion about Damar Hamlin's on-field collapse, offering a fascinating perspective on how the conversation has evolved since those uncertain early moments.

The journey continues with Episode 75's deep dive into the age-old question: what's the difference between fetishes and fantasies? Dan shares a memorable story about an uncomfortable request from a date, and we'll relive the collective shock of Tom and Gisele's divorce announcement. Finally, we'll wrap with Episode 96, featuring an early appearance by Stephanie before her current committed relationship. You'll even hear her original song she wrote for a date!

Fair warning: this episode ends rather abruptly (Bill forgot to add an outro), but after 550+ episodes, we can forgive him for that, right?

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