012: Annie’s 583 Guy Challenge

Annie is joined by her right-hand woman Caitlyn to unpack every juicy, chaotic, and unexpected moment from her record-breaking Rail Me event. From the logistics and admin nightmares to the hilarious behind-the-scenes moments (yes, including foot guy and fishing-trip virgin), they go deep into what it actually takes to coordinate an event of this scale.

Annie gets real about how she felt at every stage—from nerves at the start to the messy, emotional aftermath. Caitlyn dishes on her role, how the event ran (or didn’t), and what surprised her most. They also answer all your burning questions: How many guys? How long did each get? What went wrong? Did Annie cry? And yes... who was the very last guy?

Get ready for wild stories, unexpected emotions, and way too much detail—in the best way.

Recorded and edited by Poly Studios.

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