‘Bachelor’ Colton Underwood says Aly Raisman was his ‘first love’ and his biggest heartbreak

"It was a big step for me. It was really tough."

NEW YORK, NY - DECEMBER 12: Football Player Colton Underwood and Olympic Gymnast Aly Raisman attend the Sports Illustrated Sportsperson of the Year Ceremony 2016 at Barclays Center of Brooklyn on December 12, 2016 in New York City. (Photo by Slaven Vlasic/Getty Images for Sports Illustrated)
Colton Underwood and Aly Raisman in 2016. –Slaven Vlasic/Getty Images

Colton Underwood may only have dated Olympic champion and Needham native Aly Raisman for “seven [or] eight months” in parts of 2016 and 2017, but that didn’t stop the former NFLer and current star of “The Bachelor” from calling the gymnast his “first love.”

Underwood appeared on Tuesday’s episode of the LadyGang podcast to discuss everything “Bachelor”-related, as well as his relationships prior to the show. When asked by hosts Keltie Knight, Becca Tobin, and Jac Vanek to name the worst heartbreak he’s ever experienced, he singled out Raisman.

“While it was confusing and it was 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,” Underwood said of his relationship with Raisman. “It was a big step for me. It was really tough.”


Underwood wooed Raisman by recording a video in the summer of 2016 to congratulate her on her performance at the Rio Olympics, proposing that the two of them go on a double date with gymnast Shawn Johnson and her husband, Underwood’s former Oakland Raiders teammate Andrew East. Underwood and Raisman publicly confirmed their relationship in December 2016 when they appeared on the red carpet together at the Sports Illustrated Sportsperson of the Year ceremony, but the relationship ended in 2017.