Who Did Colton Underwood Date Before The Bachelor? His Life Before Fame Explained

Colton Underwood is back in the headlines after revealing that before finding fame on The Bachelor, he exclusively dated married men while privately struggling with his sexuality.

Speaking on the “Sibling Revelry” podcast hosted by Kate and Oliver Hudson, Underwood said he kept those relationships secret because he was not ready to publicly acknowledge that he was gay.

“I only dated married men before I was famous,” Underwood said. “I thought that was safer because there was no chance of it becoming a real relationship.”

The former Bachelor star, who came out as gay in 2021, said the arrangements reflected the fear and shame he experienced while trying to reconcile his identity before entering the public eye.

“I was living two completely different lives,” he said, explaining that he spent years trying to suppress his sexuality before eventually deciding to come out publicly.

The remarks have renewed interest in Underwood’s dating history, including his relationship with Olympic gymnast Aly Raisman and his time in the Bachelor franchise.

Aly Raisman Was Colton Underwood’s First Public Relationship

Before becoming the lead of Season 23 of The Bachelor in 2019, Underwood’s only high-profile public relationship was with Olympic gold medal-winning gymnast Aly Raisman.

The pair dated from 2016 to 2017 after meeting through a mutual friend. Underwood famously asked Raisman on a date through a YouTube video, and the two later appeared together at several public events during their relationship.

After their breakup, Underwood described Raisman as his “first love,” before eventually joining ABC’s Bachelor franchise.

From Football to Reality TV and Life After The Bachelor

Before reality television, Underwood pursued a professional football career after playing defensive end at Illinois State University. Although he went undrafted in the 2014 NFL Draft, he spent time with the practice squads of the San Diego Chargers, Philadelphia Eagles and Oakland Raiders before injuries ended his football career.

He later founded the Colton Underwood Legacy Foundation, which supports people living with cystic fibrosis, a cause connected to his family.

Following his split from Raisman, Underwood appeared on Season 14 of The Bachelorette in 2018 before joining Bachelor in Paradise, where he briefly dated Tia Booth. He was then selected as the lead for Season 23 of The Bachelor.

During the season, Underwood chose Cassie Randolph, and the couple dated for more than a year before announcing their split in 2020. Their breakup later became the subject of a legal dispute after Randolph obtained a temporary restraining order against Underwood. The matter was later resolved privately, and the restraining order was dismissed.

In April 2021, Underwood publicly came out as gay during an interview with Robin Roberts on Good Morning America, saying he had spent years trying to hide his sexuality.

He later began dating political strategist Jordan C. Brown. The couple married in 2023 and welcomed their first child, a son born via surrogate, in 2024.

Reflecting on his journey in his recent podcast interview, Underwood said he now feels able to live authentically after years of secrecy.

“I’m finally living the life I always wanted to live. There’s so much freedom in being honest about who you are.”