#915. REPEAT OUR GREATEST HIT EPISODES:

Chelsea. Freaking. Handler. The legendary comedian, best-selling author, and unapologetic queen of telling it like it is joins the pod, and NOTHING is off-limits. Chelsea gets real about turning 50 (and why she finally has the body she wanted at 20), what led her to write this new book and why men have never been the center of her story. She spills on sexting a certain governor, how stacking small wins (and rejections) led to her break in comedy, and her love of… well, you’ll have to listen. Plus, her brutally honest thoughts on cancel culture, the biggest “oops” moment of her career, and why she refuses to fit into society’s mold of what a woman should be. Get a copy of Chelsea’s new book, I’ll Have What She’s Having, available now at chelseahandler.com/book. This one is hilarious, raw, and SO Chelsea. Buckle up!

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EPISODE HIGHLIGHTS:

• (8:05) – Chelsea on why men have never been the center of her story: "You’re not my story, you’re part of the story."
• (14:40) – Turning 50: "I have the body I wanted at 20 now at 50."
• (21:17) – Chelsea’s “big break” moment: "It was a bunch of little wins stacked up."
• (24:37) – Texting with Governor Cuomo: "I went on The View to declare my love for him..."
• (47:59) – The biggest “oops” moment of her career: "I forget that my boyfriend’s stories are theirs too..."

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#914. You may think you know how American Idol works… but Gabby Barrett explains how the audition process actually goes.

This week on Off The Vine, Gabby takes us behind the scenes of Idol in a way you’ve probably never heard before — from how she was really discovered, to what happens before you ever stand in front of the judges, to competing on the show while falling for her now-husband.

After Idol, we get into the song no label wanted… before it changed her life forever and suddenly everyone started calling. We also talk about what tour life looks like with three kids, how she writes heartbreak songs from a happy marriage, and how a John Mayer quote shaped why she never reveals who her songs are about.

AND yes — there’s an embarrassingly honest confession you won’t see coming.

Trust us, this is one of the good ones ;) (get it?).

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Booking.com: Head over to booking.com and start your listing today. Get Seen. Get Booked on Booking.com!

EPISODE HIGHLIGHTS:

• (4:28) – Gabby breaks down the real American Idol audition process — what happens long before you ever see the judges!
• (7:05) – Falling for her now-husband while competing on Idol (and why she had to chase him).
• (32:15) – The song no label wanted… until everyone wanted it!
• (49:15) – An unexpectedly humbling (and hilarious) confession you won’t see coming.

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#913. In this solo episode, Kaitlyn dives into the viral “2026 is the new 2016” trend and takes a trip back to all the iconic (and messy) moments that made that year unforgettable. She talks Beyoncé dropping Lemonade, Leo winning his Oscar, Taylor Swift’s breakup with Calvin Harris, and some of the things she personally went through that year!

Nostalgia isn’t always warm and fuzzy. For Kaitlyn, it can hit like a chokehold. She gets real about online bullying, public scrutiny, and all the messy moments, but also reflects on growth, therapy, and learning how to survive it all.

Then she flips the mic to listeners. Kaitlyn answers questions and wants to know, what was your 2016 like? Comment, leave a review, and let’s get nostalgic together!

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Booking.com: Head over to booking.com and start your listing today. Get Seen. Get Booked on Booking.com!

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EPISODE HIGHLIGHTS:

• (2:10) – Diving into the viral “2026 is the new 2016” trend, laughing at old photos, and getting real about the messy, hard parts of that year.
• (8:10) – Beyoncé dropped Lemonade, Leo won his Oscar, Taylor and Calvin broke up… revisiting all the iconic 2016 moments you forgot.
• (14:20) – When looking back hurts: Kaitlyn gets real about time, memories, and growth.
• (25:30) – Answering some listener Q&A’s.
• (34:00) – Kaitlyn asks the big question: what was your 2016 like? She wants you to comment, review, and get nostalgic together.

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

#912. This week on Off the Vine, Kaitlyn is joined by stand-up comedian and internet funny guy Trevor Wallace—aka the man who perfectly captures modern bro culture, White Claw energy, and those unhinged thoughts we all have but usually keep to ourselves. He’s wildly funny, wildly self-aware, and somehow turned it all into a full-blown career.

Trevor talks about starting stand-up at 17 with zero backup plan, the viral videos the internet refuses to forget, the cease-and-desist that changed everything, and the beautifully chaotic Notes app where his funniest ideas are born. They get into dating, random celebrity airplane encounters, their shared misophonia struggle, and just riff off each other nonstop the entire episode.

You’re gonna laugh. You might gasp. You’re absolutely gonna text someone about it.

Listen or watch now!

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Thank you to our Sponsors! Check out these deals!

Covergirl: Go the distance with COVERGIRL’s new Eye Enhancer Wrap Tubing Mascara for a lash extension effect. Shop at your nearest retailer now. Only from Easy, Breezy, Beautiful COVERGIRL.com

Bombas: Head over to Bombas.com/VINE and use code VINE for 20% off your first purchase.

Pura: Right now, you can get a free Pura 4 home diffuser when you subscribe for 12 months. This offer won’t last. Get your free diffuser at Pura.com.

Progressive: Visit Progressive.com to see if you could save on car insurance!

EPISODE HIGHLIGHTS:

• (12:25) — Tried stand-up at 17… immediately decided this was the plan (there was no Plan B)
• (27:00) — The videos that changed everythin, iincluding the one that earned him a cease-and-desist!!
• (42:30) — Trevor gets real about his dating life.
• (57:08) — If he could roast anyone in the world… this is who he picks!

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#910. You may know her from the Girls Gotta Eat duo, but this time Rayna Greenberg is flying solo!

Kaitlyn and Rayna catch up on what actually makes someone sexy, dating women, and their very honest thoughts on marriage. Rayna also spills on stepping out on her own with her brand-new solo tour, Honestly, It’s You, and what it’s really like breaking away from the duo dynamic.

Things quickly spiral into conspiracy theories, bold hot takes, a surprisingly deep debate about choosing one song to listen to forever, and plenty of chaotic, unfiltered tangents you won’t want to miss.

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Thank you to our Sponsors! Check out these deals!

Covergirl: Go the distance with COVERGIRL’s new Eye Enhancer Wrap Tubing Mascara for a lash extension effect. Shop at your nearest retailer now. Only from Easy, Breezy, Beautiful COVERGIRL.com

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EPISODE HIGHLIGHTS:

• (16:15) — Rayna gets real about going solo, launching Honestly, It’s You, and what breaking away from the duo has actually been like.
• (29:30) — Rayna opens up about her dating life, “dabbling” with women, and doing what truly makes her happy.
• (40:14) — HOT TAKE ALERT: The influencer Rayna says she would not survive a day with.
• (53:00) — The “one song for the rest of your life” debate.

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#909. This week on Off the Vine, Kaitlyn gets cozy with her favorite guests… her niece and nephew, Sydnee and Brody!

While in Nashville, they kick things off by interviewing Kaitlyn — asking the questions only family can get away with — before she flips the script and dives into their world. From teenage insecurities and unexpected successes to moments Kaitlyn definitely didn’t expect to explain to family, nothing is off limits.

They share unfiltered takes on life, school, social media, and what it’s like growing up with an aunt who’s… very online. Things get heartfelt, awkward, and hilarious — especially when they wrap it up with a game of “Gas or Ass” that goes exactly how you think it will.

Tune in for laughs, life lessons, and family moments that prove some things are just better shared with the people you love.

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Thank you to our Sponsors! Check out these deals!

Covergirl: Go the distance with COVERGIRL’s new Eye Enhancer Wrap Tubing Mascara for a lash extension effect. Shop at your nearest retailer now. Only from Easy, Breezy, Beautiful COVERGIRL.com

Bombas: Head over to Bombas.com/VINE and use code VINE for 20% off your first purchase.

Ka’Chava: Rewild your nutrition at kachava.com and use code VINE. New customers get $20 off an order of two bags or more, now through the 31st!

Better Help: Off the vine listeners get 10% off at BetterHelp.com/VINE.

Apartments.com: The Place to find a place!

EPISODE HIGHLIGHTS:

• (5:06) – The kids take over. Sydnee & Brody start grilling Auntie Kaitlyn about what she was like at 18… and the most embarrassing thing she’s ever done on camera.
• (17:05) – “Everyone at school knew you…” The moment Kaitlyn realized her Hawk Tuah podcast appearance followed her straight into their classrooms
• (42:55) – Kaitlyn flips the script and makes Sydnee & Brody play a Gen Z game called “Gas or Ass”.

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

#908. This week on Off the Vine, Kaitlyn sits down with radio powerhouse Bobby Bones — and what starts as a conversation about success quickly turns into one of the most raw and unexpected episodes we’ve ever recorded.

Bobby opens up about growing up with very young parents, childhood without money, and realizing early on that he was chasing love through performance. He shares deeply personal stories he hasn’t told in years — including why vulnerability didn’t feel safe, how success complicated trust, and an unexpected act of kindness that left him emotional for days.

And yes… we go there on Dancing With the Stars! Bobby clears the air on the Mirrorball controversy, what was really happening behind the scenes, and reads a never-before-opened DM from Tom Bergeron for the first time on the podcast.

We also get into identity, rejection, why Bobby has never had a sip of alcohol, the anxiety that still keeps him up at night, and an embarrassing childhood story that’s both traumatic and hilarious.

Trust us, you’re going to want to hear this one!!

If you’re LOVING this podcast, please follow and leave a rating and review below! PLUS, FOLLOW OUR PODCAST INSTAGRAM HERE!

Thank you to our Sponsors! Check out these deals!

Covergirl: Go the distance with COVERGIRL’s new Eye Enhancer Wrap Tubing Mascara for a lash extension effect. Shop at your nearest retailer now. Only from Easy, Breezy, Beautiful COVERGIRL.

Bombas: Head over to Bombas.com/VINE and use code VINE for 20% off your first purchase.

Figs: Take 15% off your first order at Wearfigs.com with the code FIGSRX.

Quince: Go to Quince.com/vine for free shipping on your order and 365-day returns. Now available in Canada, too!

Progressive: Visit Progressive.com to see if you could save on car insurance!

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EPISODE HIGHLIGHTS:

• (9:25) — Growing up without money or Santa Claus, and what it was like being raised by teenage parents
• (14:40) — The first time Bobby ever said “I love you” — and why it didn’t happen until his wife
• (26:58) — The unexpected act of kindness from a stranger that left Bobby crying for days
• (1:11:19) — Bobby opens and reads a never-before-seen DM from Tom Bergeron about the Mirrorball controversy
• (1:20:20) — The embarrassing childhood story Bobby has never lived down — and how it still affects him today

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