"He Found Out I Went on Another Date… Now He’s Acting Weird"

"He Found Out I Went on Another Date… Now He’s Acting Weird"

April 20, 2026 · 38 min · Episode 592

About this episode

Ilana and Jake discuss dating challenges and listener questions about exclusivity.

Jake and I catch up on the abandoned 20-week challenge, our first jobs out of college, and a post-wedding brunch we hosted that actually came together really well. Then we tackle a listener question from someone who accidentally went on a Hinge date with her casual boyfriend's friend's roommate (New York City is a very small village), and help her figure out how to have the exclusivity conversation. We wrap with a round of your dating wins — from five-hour first dates to finally deleting the apps. Don't forget to follow along on Instagram to submit your dating wins! ALL links here (submit a Q, pitch yourself to the pod, dating coaching & more) Shop SKIMS Fits Everybody collection at skims.com. Rula patients typically pay $15 per session when using insurance. Connect with quality therapists and mental health experts who specialize in you at https://www.rula.com/seeingotherpeople #rulapod  Stock up on the best elevated essentials + get free shipping & 365 day returns at Quince.com/seeingotherpeople   Get $10 off your Nutrafol subscription at nutrafol.com promo code SEEINGOTHERPEOPLE See Privacy Policy at https://art19.com/privacy and California Privacy Notice at…

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SKIMS, Rula, Quince, Nutrafol

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