Soon enough, Colton Underwood will have more than twenty ladies vying for his affection — but he's no stranger to having his love life play out in the public eye. ABC's newest Bachelor [1] was a former fan favourite on Becca Kufrin's season of The Bachelorette [2], and he also stirred up some major drama [3] on season five of Bachelor in Paradise. Even before his reality TV fame, the former Oakland Raiders tight end [4] made several red carpet appearances as the boyfriend of Olympian Aly Raisman. While we're waiting for season 23 of The Bachelor [5] to begin, let's review Colton's very complicated dating history.
Aly Raisman
Even before appearing in season 14 of The Bachelorette [7], Colton's dating life was in the spotlight, as he was formerly the boyfriend of Olympic gymnast Aly Raisman. The two dated for about six months [8] beginning in 2016, after Aly concluded her 2016 Olympic season in Rio de Janeiro. After Yahoo Sports posted a video [9] of Colton congratulating her on her Olympic performance and asking her out, Aly followed up with a tweet [10] hinting she might be up for going out with the former Oakland Raiders tight end. The two eventually broke up due to the strains of their long-distance relationship [11], but Aly confirmed that they were in a "good place" and the decision was mutual.
Tia Booth
Before embarking on season 14 of The Bachelorette [12], Colton briefly dated [13] former season 22 Bachelor contestant Tia Booth. The two went on a few dates in January of 2018, the same month that Tia's season aired, but they parted way before Colton began filming his own season. However, just a few months later, the two found themselves reunited on season five of Bachelor in Paradise, where after a few will-they-or-won't-they episodes, Colton and Tia finally became an item. Tia was instantly smitten, but Colton had his reservations. After confessing to the cameras, "I can't sit around on a beach anymore and look at her every day and know that there's not a future," he broke the news to Tia and they both left Bachelor in Paradise single [14], though from Tia's Instagram posting [15], it seems it was on good terms.
Becca Kufrin
In season 14 of The Bachelorette [16], Colton quickly became a fan favourite as a contestant and a front runner for Bachelorette Becca Kufrin's affection. Colton lasted until the very end of the season, even giving Becca the chance to meet his family (and hear some majorly private confessions [17]), and it seemed like Colton might end up being The One. However, Tia Booth visited Becca on one of the final episodes to express that she still had feelings for Colton, and Becca ultimately let Colton go, telling him she just didn't see them together at the end of the journey.