Colton Underwood, who formerly played in the NFL, is The Bachelor on season 23 of the franchise’s reality dating competition. As he dates 30 women with the hopes of finding his wife, fans of the show have been curious about his past relationship history. His ex-girlfriend list is of particular interest this season because a major point on the show is that Underwood is a virgin.
Here are the women he has dated since becoming a public figure, before his start as The Bachelor:
Underwood dated US Olympic gymnast Aly Raisman from 2016-2017. Their relationship began after Underwood posted a video asking Raisman out on a double date with his Raiders teammate Andrew East and East’s wife Shawn Johnson. After the video went viral and Raisman accepted the date offer, People reported that Raisman and Underwood walked the red carpet together for the 2016 Sports Illustrated Sportsperson of the Year. Raisman told the magazine that she and Underwood had been dating since the VMAs that past August.
The two broke up in April 2017, and US Weekly reports that Underwood recently reflected on their relationship as his “first love” and “worst heartbreak.”
Following his break-up from Aly Raisman, Underwood appeared as a contestant on Becca Kufrin’s season of The Bachelorette. Underwood made it to the hometown dates as one of Kufrin’s final four men, but he was not given a rose and eliminated after bringing Kufrin home to meet his family.
When Underwood began his journey as The Bachelor, Kufrin offered her support on social media, writing “Colton, as you once told me “let’s get tonight poppin.” So go get em tiger! Excited to meet your women and have you take us on your lurve journey (drink). It’s going to be one helluva ride, but hopefully worth every second. All my love and support to you because you deserve it.”
Underwood connected with Tia Booth on Bachelor in Paradise season 5, but the two struggled because of Underwood’s indecision and he ultimately left her heartbroken on the show. After their televised break-up, Booth told People that “It’s a relief to close that chapter of my life. We’re in a good place. We’re in a solid friend zone. And it’s honestly nice to move forward instead of wanting something when it’s not there.”
Booth and Underwood had actually met before he went on The Bachelorette, and Booth was one of Becca Kufrin’s friends at the time; according to E! News, Tia went on The Bachelorette to tell Becca that she still had feelings for Colton. Booth has since moved on from Underwood, and also gave her support to him ahead of his Bachelor season premiere, writing in an Instagram caption: “Hey @coltonunderwood remember that time you wore a sleeveless sweatshirt at the beach and then we realized we were 0% compatible and solely meant to be supportive friends?… Well here’s my support. Now keep your damn shirt on and go find you a gal.”
Watch The Bachelor season 23 on ABC, Monday nights at 8/7pm CT.