Aly Raisman, the retired Olympic gymnast known for her low-key approach to romance, keeps her dating life tightly under wraps. Her dating history is relatively short. Retiring from gymnastics on January 14, 2020, after winning six medals across the 2012 London and 2016 Rio de Janeiro Games as part of Team USA’s ‘Fierce Five’ and ‘Final Five,’ Aly has still remained relevant even today as well. Embracing life beyond the gym, she enjoys exploring new interests, often sharing motivational messages on Instagram.

Now at 30, Aly Raisman reflects on her childhood expectations, admitting, “I thought that by age 30, I would be married with kids. Well, I just turned 30, and I’m single. “ Despite her current status as being “single“, Raisman has had moments in the spotlight for her romantic life, such as a memorable love story back in 2016 that stirred up gossip about her relationship with an NFL star at that time. Despite the turns of fame and fortune, Aly’s journey shows that sometimes life’s path doesn’t follow the script we envision. But who was her NFL boyfriend and how did cupid’s arrow strike through?

Aly Raisman once dated NFL star Colton Underwood

Colton Scott Underwood-Brown, an American reality television personality and former professional football player, was Aly Raisman’s boyfriend. Their romance began in August 2016 after a double date arranged by former Raiders teammate Andrew East, who is married to Olympic gymnast Shawn Johnson. After keeping their relationship private for five months, Underwood and the gold medalist went public in December 2016, making their red carpet debut at the Sports Illustrated Sportsperson of the Year Ceremony in New York.

He wrote in the memoir: “I was perfectly happy in this relationship. It was satisfying and serious. But I was keeping a secret from Aly. Though I looked like I belonged in this glitzy, glamorous world, I was broke.”But their romance ended the following summer in 2017, with Colton revealing the heartbreaking details of their breakup in his memoir, The First Time. ”

Aly FaceTimed me to end our relationship,” he recounted, recalling how he was left stunned and pulled over in disbelief. ” I pulled over to the side of the road, stunned and unable to comprehend this was happening. Aly said she felt overwhelmed, confused, and in need of a break. Afterward, I sat in my car and cried. I felt numb for days.” Aly Raisman explained at the time that she felt overwhelmed and needed a break.

Despite his attempts to reach out to her multiple times, Colton received no response to his calls or texts. Desperate for answers, he even contacted Aly’s best friend, Simone Biles, hoping for insight, but she, too, was surprised and unable to offer any explanation. “Left without closure, I went on long runs, replaying our conversations in my head, wondering what went wrong,” Colton shared.

Underwood admits the gymnastics star was his “first love”

Back in 2019, Colton Underwood candidly discussed his relationship with Aly Raisman during an episode of the LadyGang podcast. The reality TV star, 27 years old, described Raisman as his “first love,” emphasizing that their connection didn’t unfold on television but was significant, nonetheless. Reflecting on the breakup, Underwood shared, “While it was confusing and hard in the beginning, it also taught me a lot about myself—what I need, what I want, what I can do better in a relationship. It was a big step for me. It was really tough.”

Reflecting on their time together, Raisman had previously praised Underwood as “a very thoughtful person,” a sentiment that highlighted their mutual respect and admiration during their relationship. Years later, in 2021, Colton publicly came out as gay and found love with his now-husband, Jordan C. Brown. Both athletes are happy in their life now.