From Bachelorette to Vegas: Gabby Windey's Surprise Journey to Love

Sometimes the most authentic love stories aren’t the ones written by reality TV producers. Bachelor Nation alum Gabby Windey walked away from her engagement with Erich Schwer and eventually found her way to something far more genuine—a relationship with stand-up comedian Robby Hoffman that she wasn’t expecting to share so publicly, but ultimately did.

When Windey made her relationship with Hoffman Instagram official in August 2023, it wasn’t just a celebrity gossip moment. She was having a larger conversation about her own identity.“I love to stir the pot and tease, but I did want to wait until I was ready, because it is a larger conversation—because I’m dating a girl,”she said in an Instagram Story video. That kind of honesty on a platform typically designed for carefully curated content felt refreshing and real.

Hoffman, who has long been open about her sexuality, came to the relationship with her own grounded sense of self. The Brooklyn-born comedian and writer has built a career doing what she does best: being unflinchingly herself. She’s written for shows including Workin’Moms, The Chris Gethard Show, and Odd Squad, for which she earned a 2019 Children’s&Family Emmy Award. She hosts the“Too Far”podcast and has worked on projects ranging from the Canadian series Baroness Von Sketch Show to a forthcoming autobiographical series titled Rivkah in development with A24 and Showtime. That’s not a resume you build by playing it safe.

What’s particularly striking about Windey and Hoffman’s story is the speed and certainty of it all. By early 2025, they’d tied the knot during a 20-minute ceremony in Las Vegas.“Robby was literally ready to propose three weeks in, and I’m always the one pumping the brakes, but when something feels right, it just feels right,”Windey told Cosmopolitan in March 2025. In a world where Bachelor Nation relationships often feel manufactured for drama and extended media cycles, there’s something genuinely refreshing about two people who simply knew.

Hoffman’s path to self-acceptance wasn’t always easy. She was raised in the Hasidic Jewish community but eventually her family“fried out”on the lifestyle after moving to Canada. Around age 18, she was outed at a conservative school where she worried far more about losing her friends than facing her family. Her concerns weren’t unfounded—one friend told her on a Birthright trip to Israel that she couldn’t support the lifestyle Hoffman had chosen. That kind of rejection sticks, but it didn’t stop her from living authentically.

What makes Windey and Hoffman’s relationship feel different isn’t just that it’s a same-sex couple in Bachelor Nation—though that representation matters. It’s that both of them seem genuinely unbothered by the noise around them. Hoffman has always lived her life on her own terms, and Windey, after the very public dissolution of her engagement, found someone who gets that. Two people who refuse to apologize for who they are, deciding to build something together—that’s the real story here.