Kylie & Chelsea Handler on Embarrassing Vegas Nights, Flip-Flop Aversions & Bikini Skiing | Ep. 12

5 snips

Feb 27, 2025

Kylie chats with Chelsea Handler, a bestselling author and stand-up comedian known for her sharp wit on "Chelsea Lately." They dive into Chelsea's milestone 50th birthday and her quirky tradition of bikini skiing. Chelsea shares tales from her early writing days and her heartfelt essay for her nieces and nephews. The conversation takes a fun turn as they discuss her infamous aversion to flip-flops and a chaotic Las Vegas adventure, illuminating her unique perspective on aging and personal choices.

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ANECDOTE

Bikini Skiing Tradition

Chelsea Handler's birthday tradition involves skiing, often in a bikini.
This year, she rented a mountain and skied with a group of women, embodying female empowerment.

ADVICE

Embrace Aging

Embrace getting older with a "fuck it" attitude.
Confidence and self-acceptance increase with age, leading to greater happiness.

ANECDOTE

Vegas Mishap

Chelsea Handler's Vegas story involves getting lost in a dark hotel room and accidentally urinating in her shoe.
Her friend woke up to the sound, and another friend discovered the mess in the morning.

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Kylie’s back for a brand new episode of Not Gonna Lie presented by Peppa Pig and took a little field trip to New York City to sit down with today’s guest, comedian Chelsea Handler. But before Chelsea joins the show, Kylie gives an update on the fan base name (1:41) and shares her love for the Philly Phanatic in Doomscroll of the Week (2:47).

After that, the Academy Awards are coming up this Sunday but Kylie hasn’t seen a film intended for adults in months, possibly years. So instead, she honors the kids’ movies that have dominated the Kelce house for the past year in the 1st Annual Screen Time Awards (6:21)!

Then, Kylie is joined by New York Times bestselling author and hilarious stand up comedian, Chelsea Handler to talk about her big 50th birthday, her bikini skiing tradition and her excitement about getting older (13:51).

Having grown up reading all of her books, Kylie asks Chelsea about her first book “My Horizontal Life” (19:45) as well as her favorite essay in new book “I’ll Have What She’s Having” about a letter she wrote to her nieces and nephews (24:04).

Chelsea then talks about hosting “Chelsea Lately” and the time her dog Chunk once jumped out of a helicopter in an attempt to save her after she fell out (31:40). Kylie also brings up the subject of flip-flops, more specifically Jason’s flip-flops, as Chelsea has talked about her aversion to the shoes in her past stand up specials (35:20).

Lastly, Kylie asks Chelsea about her decision to not have children and why people constantly feel the need to challenge her on the matter (40:02).

Make sure you tune into More Sh*t Monday on the Not Gonna Lie YouTube channel for exclusive clips from Kylie and Chelsea's longer conversation!

Support the Show:

Peppa Pig: Shop all things Peppa Pig at Walmart: www.walmart.com/shop/peppa-pig

Chelsea’s New Book “I’ll Have What She’s Having” Available Now: https://www.amazon.com/Ill-Have-What-Shes-Having/dp/0593596579

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