Everyone the New ‘Bachelor’ Colton Underwood Has Previously Dated
To be fair, ABC’s newest Bachelor needs no introduction. Colton Underwood quickly became a fan-favorite as a contestant and frontrunner of Becca Kufrin’s season of The Bachelorette and went on to explore relationships on season 5 of Bachelor in Paradise. And prior to his Bachelor nation fame, he was an NFL player and philanthropist, as well as Olympic gymnast Ali Raisman’s ex-boyfriend. His dating rap sheet is leaving us gasping for breath.
But one thing all of Underwood’s relationships had in common? He was a contestant in a game or the guest of fame. Underwood is taking the reigns and running his own love story as ABC’s newest Bachelor. So what do the twenty-some lovely ladies vying for his heart need to know? We compiled Underwood’s dating history along with why each relationship bit the dust.
Underwood was no stranger to red carpets and press when he embarked as a contestant on The Bachelorette season 14. The former NFL player dated Olympian Ali Raisman for nearly a year from 2016 to 2017 before breaking up for unknown reasons.
Underwood showed he wasn’t afraid of the spotlight from the moment he asked Raisman out. Raisman was coming off a publicly impressive 2016 Olympic season in Rio de Janeiro when she revealed to Yahoo Sports that her fellow teammates argued over who could pick her a boyfriend first.
It was Yahoo Sports that ultimately helped land Raisman her newest relationship. They presented her with a video of Underwood asking her out and congratulating her on her Olympic performance. “Yeah, I’d go on a date with him … maybe he’ll come to the show,” she said. Raisman followed up with a tweet hinting she’d be down to meet up with the former Oakland Raiders tight end.
@Colt3FIVE thanks for the sweet video…. looking forward to meeting you :)
— Alexandra Raisman (@Aly_Raisman) August 21, 2016
Their relationship took off from there. Raisman brought Underwood alongside her to the 2016 Sports Illustrated Sportsperson of the Year Ceremony for their first official appearance. They attended the CW3PR’s Gold Meets Golden event, the 2017 Golden Globes, and the Sports Illustrated Swimsuit Launch event together as well.
“He’s been just very supportive, coming with me and keeping me company because I’m in a different hotel all the time,” Raisman said of their long-distance relationship. However, it ended up being the distance that drove them to ultimately break up.
Underwood confirmed their break up to the Peoria Journal Star in June of 2017. “We’re taking a break right now. We’re still good friends and talk, but all that travel had been a nightmare.” However, both confirmed that they were “in a good place” breaking up and that the relationship ended on good terms.
Underwood gained fame and a fan base as a front-runner on season 14 of The Bachelorette. Bachelorette Becca Kufrin immediately expressed her attraction to the former NFL player and dated him well towards the end of the season, met his family, and learned his most intimate secrets.
There was one caveat to their picture-perfect relationship that ultimately consumed their love story: Underwood previously went on a few dates with Kufrin’s close friend and former Bachelor contestant Tia Booth.
Booth visited Kufrin on one of the final episodes to express that she still had feelings for Underwood. While Kufrin reportedly didn’t take that into account amidst her feelings for the four remaining men, she did ultimately let Underwood go, telling him she just didn’t see them together at the end of the journey and wanted him to find his future partner.
Underwood dated Booth before embarking on Kufrin’s season of The Bachelorette, leading viewers to believe he may have gone on hoping that Booth was the bachelorette who’s heart he’d be competing for. The two reportedly went on a few dates in January of 2018, the same month The Bachelor aired and well before Kufrin started filming her season of The Bachelorette.
Per an interview on The Ben & Ashley I. Almost Famous Podcast, Underwood went to a December 2017 Bachelorette casting. Producers asked him to name some of his favorite women from Arie Luyendyk Jr.’s contestants on the previous season of The Bachelor, among which he named Booth. He then followed her on Instagram, she responded to his story about Stranger Things, and the rest was an odd jumbled up story told through Bachelor nation’s various shows.
While the two parted ways as Underwood went on Kufrin’s season of The Bachelorette, he revealed to Kufrin that he’d previously dated her close friend but was committed to finding love on the show. Kufrin and Underwood spent a few weeks together before she ultimately sent him home, while Booth expressed she still had feelings for her former fling.
Fast forward a few months and both Booth and Underwood show up on Bachelor in Paradise. After a few will-they-or-won’t-they episodes, the two joined together to explore their mutual love of hot dogs, Stranger Things, and rescue dogs.
It seemed their long-awaited romance wasn’t meant to be. While Booth continually expressed she was “all in” and could see her and Underwood engaged in the future, he expressed different feelings — including that he just knew she wasn’t the one and didn’t want to string her along.
“I can’t sit around on a beach anymore and look at her every day and know that there’s not a future,” he said to the camera before finding Booth for a talk.
“I think part of me wanted this to work so bad … I just wanted us to work so bad and it’s not there,” he revealed to Booth. “You deserve somebody who’s going to be crazy about you every single day.” The two cried and both left Paradise, admitting they were only there to explore their relationship with each other. They seem to have broken up on good terms, as both shared pictures to their Instagram feed wishing the other luck and love in their life.