SmartLess

Snapshot · SmartLess

"Robby Hoffman"

Explore episode Aug 10, 2026

Where this was said

Gabby Windey: The Bachelorette Who Married the Comedian

At 37:25 · chapter starts 34:55

Sean Hayes drops the revelation: Robby's wife Gabby Windey was the Bachelorette, arriving with 25 male contestants before ultimately ending up with Robby. The line — 'my wife had 25 boyfriends four years ago, and I got the final fucking rose in the end' — brings down the room. Robby recounts Gabby's backstory: she had gay thoughts when she was younger but her parents were so anti-gay that she suppressed them and pursued relationships with men, which was easy because she could. On The Bachelorette, she worked one shooting day per week while spending the rest of the time in Europe with the other women — which Robby drily notes sounds like its own gay awakening. As the field narrowed, Gabby realized she didn't feel it for any of the remaining men. They met outside a bar in LA after Robby's stand-up, when a fan spotted Robby at the exact right moment, allowing Robby to perform casual generosity within earshot of the very attractive woman next to her. Their banter was immediate. They've been together four years and married in Las Vegas for $799 — limousine, officiant, photographer included.

Society & Culture
The Bachelorette Who Married the Comedian

"Robby Hoffman" · Aug 10, 2026 Society & Culture

Gabby Windey was the Bachelorette with 25 male contestants. Robby met her waiting for a Uber after a comedy show and got spotted by a fan at the perfect moment. Their banter was excellent immediately.

Society & Culture
$799 Vegas wedding

"Robby Hoffman" · Aug 10, 2026

Robby and Gabby married in Las Vegas for $799, a package that included a limousine, an officiant named Reverend Nature, and a photographer named Nathan.

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