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'Coming Out Colton': All the women 'The Bachelor' star Colton Underwood has dated

Before coming out as gay, Underwood dated quite a number of famous women
Cassie Randolph (L) and Colton Underwood attend the 2019 MTV Movie and TV Awards (Photo by Emma McIntyre/Getty Images for MTV)
Cassie Randolph (L) and Colton Underwood attend the 2019 MTV Movie and TV Awards (Photo by Emma McIntyre/Getty Images for MTV)

For former football player and reality star Colton Underwood, coming out wasn't easy. After having been blackmailed, Underwood chose to live authentically as himself. Now, in a new Netflix docuseries titled 'Coming Out Colton', he opens up about his journey. But before you sit down to watch the 6-part series, here's a look at some of Underwood's relationships.

If you're looking for other docu-series, you might want to check out titles such as 'Adrienne', 'Myth & Mogul: John DeLorean' and 'Luke Bryan: My Dirt Road Diary'.


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Aly Raisman

Back in 2016, Underwood dated gymnast and two-time Olympian Aly Raisman. The manner in which he asked her out was rather cute, seeing that he asked her in a video that went viral while she was competing in the 2016 Summer Olympics. The pair later met in Denver, Colorado.

They began dating shortly after, but during this time, Underwood was broke. He opened up about the same in his book, 'The First Time'. Having spent most of his money on his shoulder surgery and the rest to fund his trips to see his girlfriend, he had little to no money left. However, in 2017, Raisman and 18 others opened up about the sexual abuse they faced at the hand of Larry Nassar, the former USA Gymnastics team doctor.

That year, Raisman broke up with Underwood, as the case went public. Underwood in his book mentioned that he understood what was happening with Raisman was bigger than him and wanted to support her regardless. "And as much as the split hurt me, I decided all I could do was support her unconditionally and pray she could one day heal those wounds and make sure she knew I would always treasure the time we did have together," he wrote.


Savannah Chrisley

After his breakup with Raisman, Underwood was left heartbroken. In order to deal with it, he found himself having a 'good time' with reality star Savannah Chrisley, as he spoke about it on 'The Bachelor' blogger Reality Steve's podcast. "After dating Aly, a couple weeks went by and I was sort of in a funk and didn't know if I was going to put myself out there again," he explained. "Then her and I start talking on social media. And next thing you know I'm in Vegas at the ACM's." he added. But Underwood was serious about not wanting anything serious whatsoever. 

"I was very clear, I was like I'm down to meet. I'm down to have a good time. I just got out of a serious relationship and I don't want to walk the carpet." he added. "I don't want to be photographed together. But I'll come meet you and your friends." he said.


Becca Kufrin

For Underwood, a significant amount of fame came when he was a part of Becca Kufrin's season of 'The Bachelorette', seeing that he was already a familiar face by then. Underwood made it quite far on the show, seeing that he entered the series' all-important hometowns segment, where Kufrin met with his family. However, he did not end up with a rose, causing him to be eliminated and ending their romance. However, he continued to be friends with her and her then-fiancé Garrett Yrigoyen. Underwood and Yrigoyen grew close during their time on the show, and Kufrin even opened up about how easy their friendship was. "I think it's an easy dynamic," Kufrin told Us. "I think people think it's weird to stay friends with people you've dated, but it's been fine for us. We've stayed close with him since my season ended." she added, talking fondly about Underwood.


Tia Booth

Although Underwood tried to win Kufrin's heart on the show, he was allegedly involved with fellow 'The Bachelor' nation alum, Tia Booth. Before his run on Kufrin's season, the two allegedly spent time together, which led to Booth telling Kufrin how she still had feelings for Underwood. Booth and Underwood then went on to star in the spin-off series 'Bachelor in Paradise'. Unfortunately, they didn't last very long, with Underwood claiming that he still had feelings for Kufrin.


Cassie Randolph

After the Kufrin-Booth love triangle, Underwood starred in his season of 'The Bachelor'. With Cassie Randolph having won his heart, she received the final rose but no engagement. However, Underwood did lose his virginity to Randolph as he mentioned in his book, 'The First Time'.

In a chapter titled 'What Happened in the Fantasy Suite', Underwood wrote -- "None of your business." However, he did mention that a glass shower in the room meant that "going to end up naked in front of each other". And while their relationship was all rosy on camera, it certainly wasn't smooth coming off the season. They had quite a messy breakup, with Randolph filing a restraining order against him. She had also previously accused him of stalking her. 


'Coming Out Colton' premieres on December 3, 2021 on Netflix