After time on The Bachelorette and Bachelor in Paradise, Colton Underwood gave fans a lot to talk about this Bachelor season. However, he has a dating history beyond reality TV. And yes, that includes another famous ex, even though he's been respectfully quiet about their relationship. In fact, Underwood dished his relationship with Aly Raisman on the LadyGang podcast's Jan. 15 episode.
During the discussion, the Bachelor referred to the Olympic gymnast as his "first love," as pointed out by E! News. He told the podcast hosts that he dated her for "seven or eight months." Even so, Underwood described their breakup as his "worst heartbreak." At least that breakup wasn't filmed by reality TV cameras, right?
He reflected, "While it was confusing and hard in the beginning, it also taught me a lot about myself." That breakup helped him realize "what I need, what I want, what I can do better in a relationship."
Even though this relationship didn't play out on reality television, it was still pretty public. In fact, it was very public before it even began. In 2016, Underwood recorded a video for Yahoo! Sports praising the gymnast for her accomplishments at the Olympic Games in Rio. Instead of just posting that video, Yahoo! Sports shared a video of Raisman watching Underwood's video.
And at the end of his message, he decided to take a chance and ask her out. Colton said, "If you're ever in San Jose and want to go on a double date with me, Andrew, and Shawn, let me know." And by Andrew and Shawn, he meant Olympian Shawn Johnson and her husband Andrew East, Underwood's former teammate on the Oakland Raiders.
After Raisman watched Underwood's message, she revealed to Yahoo! Sports, "They've actually told me about him before. He's very cute." Clearly, Johnson and East were trying to set this up for a bit. She also remarked, "I would go on a date with him." And spoiler alert: She did.
In a 2016 interview with People, Raisman confirmed their romance and talked about the progression of their relationship. She revealed, "We happened to both be in Denver at the same time. I was there for less than 12 hours, he was flying in for just a few days. It just ended up working perfectly.”
In that same People interview, Raisman revealed that he drove 90 minutes back and forth to meet her for their second and third dates. This guy is all about traveling for love. First with Raisman, and then hopping on planes (and helicopters) on the Bachelor franchise.
In February 2017, the then-couple discussed their Valentine's Day date during a red carpet interview with Access. She shared,
"He cooked me dinner that night because we were supposed to go out for dinner. I didn't want to complain. I was gonna rally. I was tired."
That same year, they both shared Valentine's Day posts on social media. In his post, Underwood shared a photo of himself looking on while she did interviews.
That same Valentine's Day, Raisman shared a photo of herself with roses (not from a rose ceremony), a gift bag, and a giant teddy bear.
Even though Underwood hasn't dished too much on his past relationship with Raisman, he handled the intrigue with both class and honesty. As tough as that heartbreak may have been, everything happens for a reason and it prepared him for dating in the spotlight on The Bachelor.