#859. Kaitlyn is joined by one of the most iconic men in Bachelor history—Ben Higgins—to unpack the chaos, chemistry, and unseen moments from their unforgettable season. From how a coworker convinced him to apply for the show, to the Fantasy Suite date that ended with Ben accidentally destroying a $50,000 antique desk, this episode is full of stories you’ve never heard—until now!!

They revisit all their standout moments—from two-stepping at the honky-tonk to the sex-ed date that made America swoon—and share the story of the night they told each other “I’m falling in love” … a moment Kaitlyn thought was about to turn into a virgin confession (spoiler: it didn’t). And just when you think you've heard it all—Ben reveals that Kaitlyn mooned him through a window after he was sent home… something she has zero memory of. You truly can’t make this stuff up!

They also catch up on life today, and how Ben is now truly living out the prayers he once whispered—as a husband and brand-new father. You have to hit play. This one’s unreal!

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EPISODE HIGHLIGHTS:

• 7:05 – How a coworker convinced Ben to apply for The Bachelorette!
• 24:47 – The “I’m falling in love” moment Kaitlyn thought was a virgin confession.
• 28:30 – The Fantasy Suite disaster that destroyed a $50K antique desk!
• 51:08 – Ben reveals Kaitlyn mooned him through a window after she sent him home.
• 58:58 – How the show changed Ben’s life—and the prayers he’s now living as a husband and father!

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#858. Fan favorite Jared Haibon joins Kaitlyn for this week’s Bachelorette rewatch, and they cover it all. He gets called out for voting for Britt (yep, still regrets it), relives the group date that left him with a black eye, and breaks down their most iconic moments — including a live Cranberries performance in a castle.

They dive into sleep deprivation, fashion fails, and a whole lot of movie quotes. Jared also opens up about being a late bloomer, his rollercoaster with Ashley Iaconetti, and how a floaty and a Titanic-level move finally sealed the deal on their real-life love story.

It’s funny, nostalgic, and a must-listen. Full episode out now!

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Figs: Right now, if you go to wearFIGS.com and use the code FIGSRX, you can get 15% off your first order.

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Better Help: This episode is brought to you by Better Help. Off The Vine listeners get 10% off their first month at BetterHelp.com/VINE.

EPISODE HIGHLIGHTS:

• 3:30 – Jared on why he voted for Britt... and why he still regrets it!
• 21:35 – Jared on Nick Viall: “He’s my dick” — the hilarious way he describes their bromance!
• 37:29 – The Cranberries. A castle. Ireland. Jared and Kaitlyn’s most unforgettable date.
• 55:13 – Jared breaks down his love story with Ashley Iaconetti: a floaty, the Titanic moment, and the big “I love you”!

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#857. He Drove Up in a Cupcake and Drove Off with Our Hearts! Kaitlyn is joined by the one and only Chris “Cupcake” Strandburg for a trip down memory lane through her entire season of The Bachelorette. From being the first kiss on night one to reminiscing on group dates in Ireland, Chris shares the wildest behind-the-scenes stories — including how he landed the iconic cupcake-mobile (yes, it involves Burning Man), hilarious moments from the Aladdin group date, and how Kaitlyn rode off into the sunset in two helicopters… while he took a three-hour bus ride back. He spills on Amy Schumer, almost being cast on Andi Dorfman’s season, and even shows up with actual Bachelor memorabilia!! Nostalgic, hilarious, and unexpectedly sweet — this reunion is one for the books.

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Quince: Go to QUINCE.com/vine to get free shipping and 365-day returns.

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Better Help: This episode is brought to you by Better Help. Off The Vine listeners get 10% off their first month at BetterHelp.com/VINE.

Splendid: Right now, Splendid is offering our listeners 20% off when you go to Splendid.com and use promo code VINE at checkout or when you shop at Splendid in stores.

EPISODE HIGHLIGHTS:

• (9:16) Chris reveals he was originally cast for Andi Dorfman’s season — and why he turned it down.
• (12:38) The full story behind the cupcake entrance that made Bachelor Nation fall in love.
• (23:09) Wait… WHO did Chris meet before filming? The wild “don’t steal my girl” moment with a future castmate.
• (41:12) Behind the scenes of the Aladdin Broadway group date!
• (58:41) Cupcake comes bearing memories: a dried-up rose, a mini cupcake replica, and an actual tabloid cover.

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