There’s nothing better than a Bachelor contestant with Bachelor Nation ties! Gabby Windey dated two members of Bachelor Nation before her journey on Clayton Echard’s season of The Bachelor led her to become one of the newest Bachelorette leads.
“We like the same girls, man. I didn’t know Dean until obviously, like, 2018, but Gabby was a good friend of one of my very good friends from college, they were roommates,” the Bachelorette season 14 runner-up said on his “Behind the Rose” podcast at the time. “I met Gabby long before I was on The Bachelorette, like, I want to say maybe 2015 or 2016. We hung out for a little bit, so I know her very well. And Dean, I don’t know how it came up, but one time, me and Dean were sitting there — I think we were in Buffalo, and he mentioned Gabby — and I was like, ‘How do you know Gabby?’ And he was like, ‘Dude, she was, like, my girl in college, you know, we were in love and blah blah.’”
Blake, who hooked up with Dean’s girlfriend, Caelynn Miller-Keyes, before they all appeared on Bachelor in Paradise season 6 in 2019, noted at the time that he dated Gabby “for a couple months.”
“She’s fun. She has a very outgoing personality, very loud, like, when she walks into a room, you know she’s in a room,” he added. “You never know if the lead is going to be into something like that. You never know if they like the more shy, quiet type or they like the loud, outgoing type, but she’s definitely very loud, very outgoing, she has a lot of friends. So if Clayton’s into that, I see her getting hometowns, for sure. She’s a beautiful woman. … They’re gonna have the football player, cheerleader story line.”
Dean, for his part, didn’t name names when discussing his ex on his “Help! I Suck at Dating!” podcast in October.
“She was, like, one of the main exes. She was my girlfriend from college,” he said. “Producers called me and were like, ‘Hey, we’re thinking of casting this person — what do you think of her? We know that you dated 10 years ago.’ And I was like, ‘Oh, she’s great. If she gets selected for the show, she’ll either win the show or she’ll be the next Bachelorette.’ And I firmly believe that.”
Gabby later set the record straight about her past dating history with Bachelor Nation. On an episode of the “Talking It Out With Bachelor Nation” podcast, Gabby claimed her previous romance with The Bachelorette season 14 runner-up wasn’t as serious as he may have indicated.
“We never actually went on a date. There was no drinks paid for. No dinner paid for. [Blake’s] saying we dated,” Gabby told cohosts Mike Johnson and Bryan Abasolo in January 2022. “He’s definitely friends of friends. 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.”
Her past romances, didn’t keep her from building a strong relationship with Clayton. During the February 28 episode, Gabby earned her spot in the final three alongside Susie Evans and Rachel Recchia. However, Gabby and Rachel were both sent home so Clayton could reconnect with Susie Evans amid her departure.
In March 2022, host Jesse Palmer revealed during After the Final Rose that Gabby and Rachel were named co-leads of season 19 of The Bachelorette. This is the first time in the franchise’s history that two leads will appear side by side for the entirety of a season.
“I am so happy for her. I truly am!” Rachel said during the After the Final Rose special. “It’s crazy. This is insane and I’m excited to do this journey with you. We did it once together. We’ve been through the most crazy experience together.”
Gabby chimed in: “I’m a girl’s girl through and through, so having a friend by my side is the best thing I could ask for.”
The Bachelorette airs on ABC Mondays at 8 p.m. ET.