Chelsea is looking for a man who’s not afraid of her ambition, her intensity … and her job as a real-life break-up coach. Will any of Jujubee’s picks create a spark with Chelsea, or will they all burn out?
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Mar 2021
Jessica: Going In For The Rebound
With a cheating ex in her past, 28-year-old Jessica is ready to meet a guy who’ll treat her right! Will it be Jordan, a teacher’s assistant who has trouble locking down first dates? Or Logan, an actor who’s always been first to call it quits in a relationship…? Learn more about y ... Show More
23m 50s
Nov 2020
Natalia: Stuntwoman Seeks Leading Man
With a dating past marked with tragedy, 24-year-old Natalia is taking nothing for granted. She’s looking for a goal-oriented guy with an edgy sense of humor… Will she find it in Ryan, 24, a gamer looking to take the adventure offline? Or will Bennett, 25, an open-minded jacuzzi-e ... Show More
23m 4s
Apr 2025
Chelsea Handler Ghosted by Andrew Cuomo?!
Chelsea Handler joins U Up? for a hilarious deep dive into her dating history—celebrities, non-celebrities, and even a near-miss with Andrew Cuomo. She spills the tea on how the former governor slid into her DMs (but didn’t seal the deal), the power players she’s dated, and why s ... Show More
56m 18s