Former 'Bachelorette' Star Gabby Windey Has a Girlfriend — Who Else Has She Dated?

Gabby Windey has made Bachelor franchise history in two significant ways. First of all, she and Rachel Recchia became the first double Bachelorettes in Season 19 of the popular reality dating show.

Then in August 2023, Gabby revealed she was in a relationship with a woman. Before we get to know her new lady love, let's revisit Gabby's dating history. It's a real Bachelor throwback.

Fans of The Bachelorette might remember Dean Unglert from Season 13 although the more memorable aspect of that run was Rachel Lindsey, the show's first Black Bachelorette. Dean didn't make it past week 8 but he did show up in a few of the spinoffs. Before he moved into Bachelor nation, Dean and Gabby dated in college.

"I dated Dean, so like, over 10 years ago. I think we were 18, 19 ... in college. He’s one of my first loves," Gabby revealed in January 2022 while guesting on the Talking It Out With Bachelor Nation podcast. "We are both really supportive of each other," she said, referring to Dean as a "friend."

Gabby has also been linked to Season 14 Bachelorette contestant Blake Horstmann, although she tells a different story. On his podcast, Behind the Rose with Blake Horstmann & Erik Bradley, Blake alleges he and Gabby dated for a couple of months in 2015 or 2016. "We hung out for a little bit, so I know her very well," said Blake.

Back to the Talking It Out podcast, Gabby said she and Blake never actually went on a date. "You know, we had spent time together and stuff but definitely no, like, official dating, like, no really kind of formal, no exclusivity and again, it was a really long time ago," she said. Gabby was then engaged to Erich Schwer, who was a contestant on her season of The Bachelorette, but they called it off in November 2022. Both stated they just weren't right for each other. Now we know why.

Gabby and Rachel made it to the top three in Season 26 of The Bachelor but Clayton Echard ultimately chose Susie Evans, although they broke up in September 2022. When Gabby was told she and Rachel would be sharing the Bachelorette spotlight in Season 19, she said, "I’m a girl’s girl through and through, so having a friend by my side is the best thing I could ask for." It turns out Gabby really is a girl's girl.

On Aug. 2, 2023, Gabby went on The View and shared she was dating a woman. While excitedly clapping for herself, which we love to see, Gabby bounced up and down after making the big announcement. When View co-host Sunny Hostin said she didn't see this coming, Gabby said she didn't either. "I think it was always a whisper in me that just got louder and louder," said Gabby.

So, who is Gabby's new girlfriend? She is dating comedian Robby Hoffman. The two made it Instagram official the same day Gabby went on The View. Robby posted a carousel of photos with Gabby and tagged her in the caption. "Baby!!!" responded Gabby in the comments. Over on Gabby's IG, she did the same with a callback caption that read, "Told you I’m a girls girl!!"

A link on Robby's Instagram takes us to a bio for her appearance at Zoofest which is part of the Just For Laughs comedy festival in Montreal. She describes herself as a "small ex-Hasidic queer Jewish stand-up comedian, writer, and true original." Robby was also "named one of Vulture's Top Comedians to Watch in 2020, one of Comedy Central's UP NEXT comedians, and was on Conan O’Brien’s Comics to Watch list."

In a February 2020 interview with the Jewish Journal, Robby talked about how she found standup comedy. Because of her strict upbringing, Robby wasn't familiar with the standup comedy scene of the '80s and '90s. "I had this unique experience of falling in love with stand-up [while] at the same time learning about it," she told the outlet.

She began doing comedy in 2012 and has since recorded a one-hour stand-up special called I'm Nervous. Robby has also "provided her TV talent in the writers’ rooms of The Chris Gethard Show, the Netflix series Workin’ Moms and PBS’s Odd Squad, for which she received a Daytime Emmy Award in 2019.

Thankfully, Robby finally decided to start a podcast with fellow comedian and writer, Rachel Kaly. On Too Far with Rachel Kaly and Robby Hoffman the two mostly talk s--t. We can't wait to smash that subscribe button. Here's hoping Gabby is a guest at some point because we gotta know how this romance bloomed.