Michael Rapaport joins Chelsea this week to discuss Kanye West, getting better at relationships with age, and marrying the one that got away. Then: A liberal mom wonders if she needs to ditch her problematic f-buddy. A comedian lacking confidence struggles to prepare for their next big show. And a 30-something is caught between two men - who both happen to be in love with her.

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Need some advice from Chelsea? Email us at DearChelseaProject@gmail.com

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Executive Producer Nick Stumpf

Produced by Catherine Law

Edited & Engineered by Brandon Dickert

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Not Wearing Pants with Michael Rapaport 01:03:11 Share

Life Will Be the Death of Me with Chelsea Handler

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Not Wearing Pants with Michael Rapaport