Kaitlyn Bristowe Dating History: Boyfriends, Engagements

Kaitlyn Bristowe had an impressive dating history even before becoming season 11’s The Bachelorette star in 2015. While she initially found love with Shawn Booth followed by a long engagement, the Leduc, Canada, native got engaged a second time to Jason Tartick, a contestant from season 14 of the ABC reality show.

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Jason and Kaitlyn have fought off breakup rumors multiple times since he proposed in May 2021. The most recent came in July 2023, when fans noticed the pair were taking separate beach vacations and she wasn’t wearing her engagement ring in a series of Instagram bikini photos. However, Jason mentioned the pair had busy schedules for the month that were going to keep them apart. Kaitlyn’s getaway was for a girlfriend’s bachelorette party, so naturally her fiancé wouldn’t likely have been in attendance. However, the duo announced their split in August 2023 following rampant fan speculation.

Shawn Booth

The Connecticut native received Kaitlyn’s final rose on the season 11 finale of The Bachelorette, as Kaitlyn accepted his romantic proposal.

From the very beginning, the dance teacher said she knew Shawn was the one for her. “I actually thought I knew night one and I just hoped from that moment on. I think I made the mistake of admitting it was him from night one [to producers],” she said in a 2017 interview, adding, “I said right away, ‘Game over. It’s that guy, no questions.’”

Shawn revealed in 2018 that the couple was in no rush to get married, explaining, “We have our own stride with how we want to take our relationship from the show out into the real world and it really has been an adjustment. But we’ve always been on the same page. We click like that. We’ve been normal and want to keep that normalcy.” The pair broke up later that year, announcing in a joint statement that they had “evolved as people, which is taking us in different directions.”

Jason Tartick

The banker competed for Becca Kufrin‘s love on season 14 of The Bachelorette but was sent home in week nine. One woman’s loss was another’s gain, as Kaitlyn fell for Jason after he appeared on an episode of her “Off the Vine” podcast shortly after her split from Shawn. In January 2019, the pair were photographed going out on several dates and made their relationship Instagram official on Valentine’s Day.

Their whirlwind romance saw Kaitlyn and Jason move in together in June 2019, and created a furry family by adopting two golden retrievers. She told Life & Style exclusively in October 2020 that they would likely get married, and that Jason would take the lead in wedding planning.

“He’s a good planner. I’m terrible at all that stuff,” she admitted. “We’ve talked about [location]. It’s so funny because he’s so proud of where he comes from and he genuinely wants to get married in Buffalo, New York, where he’s from with all our family and friends so we’ll see. I’m not against anything,” she revealed.

Jason popped the question in May 2021, presenting his new fiancée with a 5-carat, oval-shaped diamond set on a gold band. At the time Kaitlyn gushed, “It was everything I could have asked for,” about his proposal. By October 2022, things were still moving slowly when it came to walking down the aisle, as she revealed, “We need the venue and date first. We are both kind of stressed out to be honest with you.”

Kaitlyn and Jason broke off their engagement, though, and split in August 2023.