The pair met while competing against one another on season 31 of Dancing With the Stars in fall 2022. The former Bachelorette went on to finish in second place while the Jersey Shore star came in seventh. When Windey made it to the finale of the competition, Guadagnino congratulated his competitor and referred to her as his “baby mamma” to which the ABC personality replied, “My main man.”
Rumors swirled of a potential romance between the TV personalities after Windey broke her silence on her split from Erich Schwer — whom she got engaged to during the September finale of The Bachelorette. The former couple announced they called off their engagement two months later.
“The end of our relationship happened because we weren’t completely in step and in sync with each other in our common goals or just the way we approach life,” the former ICU nurse revealed to her DWTS partner, Val Chmerkovskiy, during a November episode of the competition series.
Windey later addressed the playful banter going on between herself and the MTV personality while appearing on a November 2022 episode of the “Chicks in the Office” podcast.
“I mean, we’re friends. We were on [Dancing With the Stars] together,” she explained at the time. “Apparently both of us just like to kind of stir the pot. Which is, like, funny. But [the rumors] did happen out of nowhere.”
Windey noted she found it “hilarious to watch” the public frenzy over her and the Chippendales star’s goofy remarks on social media. “All of a sudden … everybody’s blowing up in the comments,” she said at the time, joking that she was prepared to be a “Guido in training.”
A few days later, the former NFL cheerleader exclusively told Us Weekly that she would be open to going on a date with the New York native stating that she “could use a pick me up.”
The twosome’s playful banter continued on social media following the finale of DWTS. Guadagnino took to Instagram in late November to share a photo of himself captioning the photo, “If I’m a lot, go find less.” Windey replied: “A lot of you is never enough.”
While on the red carpet for the 2022 People’s Choice Awards in December, the Illinois native shared exclusively with Us that she would be open to the “possibility” of a potential romance with the Jersey Shore Family Vacation star.
“I think it’s a possibility. I don’t know, we’ll have to wait and see,” Windey replied at the time. “Gabby, tan, laundry,” she joked, referring to the MTV series’ famous “GTL” tagline, “Gym, tan, laundry.”
After months of speculation, Guadagnino admitted that he’d be interested in going out with Windey. “I would take her on a date one day, there it is,” he told Entertainment Tonight in January 2023. “We’re both comedians, so that’s where you get a lot of the banter. … But I think that we do have good chemistry and I would take her on a date. We just haven’t had the chance at all.”
The reality star teased that the timing hasn’t lined up for the duo to take a chance on romance. “She was doing the show and I lost. Next thing you know, she’s on [the DWTS] tour,” he added. “It’s complicated, but she’s an awesome person.”
Scroll down for every flirty encounter between Windey and Guadagnino: