History of Colton Underwood in Timeline

By Popular Timelines Editorial Team · Updated: February 27, 2026

Colton Underwood is an American reality television personality and former professional football player. He played in the NFL as a defensive end after playing at Illinois State. He gained wider recognition as a contestant on the 14th season of The Bachelorette before becoming the lead of the 23rd season of The Bachelor. Notably, he is the first lead in The Bachelor franchise to publicly come out as gay.

Sections (3)

Full Timeline Early Life & Education Career & Achievements

January 26, 1992: Colton Underwood's Birth

On January 26, 1992, Colton Underwood was born as Colton Scott Brown-Underwood.

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2010: Graduation from High School

In 2010, Colton Underwood graduated from Washington Community High School.

May 10, 2014: Signed by San Diego Chargers

On May 10, 2014, Colton Underwood was signed as an undrafted free agent by the San Diego Chargers.

September 23, 2014: Returned to Chargers

On September 23, 2014, Colton Brown-Underwood returned to the Chargers and was signed to their practice squad.

2014: Signed by San Diego Chargers

In 2014, Colton Underwood was signed as an undrafted free agent by the San Diego Chargers.

September 5, 2015: Waived by San Diego

On September 5, 2015, Colton Underwood was waived by San Diego.

December 1, 2015: Signed to the Oakland Raiders' practice squad

On December 1, 2015, Colton Underwood was signed to the Oakland Raiders' practice squad.

January 2016: Founded Colton Underwood Legacy Foundation

In January 2016, Colton Underwood founded the Colton Underwood Legacy Foundation to raise money for cystic fibrosis research and medical equipment.

August 29, 2016: Released by the Raiders

On August 29, 2016, Colton Underwood was released by the Raiders.

2016: Used Grindr Under Alias

From 2016, Colton Underwood stated that he used the dating app Grindr under an alias.

2016: Started Dating Aly Raisman

In 2016, Colton Underwood started dating gymnast Aly Raisman after asking her out in a video.

2017: Used Grindr Under Alias

From 2017, Colton Underwood stated that he used the dating app Grindr under an alias.

2017: Ended Dating Aly Raisman

In 2017, Colton Underwood and Aly Raisman ended their relationship.

January 2018: Legacy Project began

In January 2018, the foundation began the Legacy Project, with the goal of delivering AffloVests to children in 50 US states.

September 4, 2018: Announced as the star of 'The Bachelor'

On September 4, 2018, ABC announced that Colton Underwood would star in the 23rd season of 'The Bachelor'.

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September 21, 2018: Filming for 'The Bachelor' began

On September 21, 2018, ABC announced that Colton Underwood had started filming 'The Bachelor' and met three contestants on 'The Ellen DeGeneres Show'.

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November 2018: Started dating Cassie Randolph

In November 2018, Colton Underwood began dating Cassie Randolph after meeting her on season 23 of 'The Bachelor'.

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2019: Blackmailed into coming out

In 2019, Colton Underwood was blackmailed into coming out after an anonymous man threatened to reveal a nude picture of him taken at a gay sauna.

May 2020: Ended relationship with Cassie Randolph

In May 2020, Colton Underwood and Cassie Randolph ended their relationship.

September 2020: Cassie Randolph filed a restraining order against Underwood

In September 2020, Cassie Randolph filed a restraining order against Colton Underwood, alleging stalking and harassment. She claimed he stalked her outside her Los Angeles apartment and her parents' Huntington Beach house, sent harassing text messages using an anonymous number, and installed a tracking device underneath her car.

April 14, 2021: Production for Netflix unscripted series

On April 14, 2021, Variety reported that Colton Underwood was in production for his own unscripted series at Netflix.

September 1, 2021: Reported dating Jordan C. Brown

On September 1, 2021, Colton Underwood was reported to be dating Democratic strategist Jordan C. Brown after they were spotted vacationing together in Hawaii.

December 3, 2021: 'Coming Out Colton' premiere

On December 3, 2021, the six-episode series 'Coming Out Colton', produced by Jeff Jenkins, premiered on Netflix. The series received major criticism.

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December 2021: Confirmed relationship with Jordan C. Brown

In December 2021, Colton Underwood confirmed his relationship with Jordan C. Brown in a birthday post for Brown.

February 2022: Engaged to Jordan C. Brown

In February 2022, Colton Underwood confirmed that he and Jordan C. Brown had gotten engaged shortly after his 30th birthday the previous month.

May 13, 2023: Married Jordan C. Brown

On May 13, 2023, Colton Brown and Jordan C. Brown were married.

May 21, 2024: Announced expecting a baby

On May 21, 2024, it was announced that Colton Underwood and his husband were expecting a baby via egg donor and surrogate, in an interview with Men's Health magazine.

September 26, 2024: Welcomed first child

On September 26, 2024, Colton Underwood and Brown welcomed their first child, a son named Bishop.

2024: Competed in 'The Masked Singer'

In 2024, Colton Brown-Underwood competed in season eleven of 'The Masked Singer' as "Lovebird" and was eliminated on "Transformers Night".

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August 18, 2025: Co-hosted dating reality series

On August 18, 2025, Colton Brown-Underwood co-hosted alongside Kaitlyn Bristowe on a dating reality series titled, Are You My First? Featuring twenty-one virgin singles that premiered on Hulu.

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