Meet All Colton Underwood’s Girlfriends From Aly Raisman to Cassie Randolph

Famous American reality television personality Colton Underwood came out as gay in April 2021. But before then, he had been in relationships with several women, including Savannah Chrisley (2017), Aly Raisman (2016 – 2017), Tia Booth (2017 – 2018), Becca Kufrin (2018), and Cassie Randolph (2019 – 2020).

Before he ventured into reality TV, Colton pursued a career in professional football but later gave it up in August 2016 to embrace a career on television, beginning with the 14th season of the reality television dating game show, The Bachelorette. Since then, his love life has been an open book to everyone; or so did many believe until he publicly came out as gay in April 2021.

It has been suggested in some quarters that he is only claiming to be gay to avoid the heat coming from his past heterosexual relationship with Cassie Randolph who got a restraining order against him, accusing him of manipulative and abusive behavior. But The Bachelor star is already recognized as the first lead in the history of the franchise to come out as gay and was recently seen on vacation with a man who is said to be his lover. All of these have had people revisiting Colton Underwood’s relationship history.

The Former American Footballer Is Currently Dating Jordan C. Brown

In early September 2021, roughly four months after the reality TV star came out as gay, it was reported that he was spotted on vacation in Hawaii with a man who was later revealed to be Jordan C. Brown. As it was reported, Colton and Jordan were all cozy and publicly displaying affection for each other that there was no doubt they are lovers.

This left a lot of people curious about who his partner is and it was only a matter of time before it was uncovered that he is the former boyfriend of the American contemporary artist, Paul Rusconi. From what we gathered, Jordan and Paul had been dating since 2017 and broke up sometime in early 2020. When Colton and Jordan began their relationship is yet to be confirmed.

Jordan is a political strategist who looks for ways to channel politics, technology, and entertainment towards facilitating social change. He graduated from Stanford University in 2004 with a BA degree in Political Science/English. The same year, he worked as a Field Organizer in Portland, Oregon, for the John Kerry presidential campaign.

Since then, he has worked with various notable establishments like Cancer Schmancer Movement, Summit Series, X Prize Foundation, and SB Projects, LLC. Brown founded JCB Consultiong LLC based in Greater Los Angeles Area in 2010. He is also the founder of One Blue Hill, a firm based in Los Angeles as well. He describes the company as a boutique political strategy agency that works with clients from diverse fields to achieve innovative advocacy and philanthropy.

A California native, Jordan lives in Los Angeles with Paul and is very fond of the artist’s two kids. If this has changed, his Linkedin profile is yet to reflect it as of the 28th of September 2021.

All The Women Colton Underwood Dated Before He Came Out of The Closet

1. Cassie Randolph (2019 – 2020)

Colton Underwood and Cassie Randolph met on the set of the 23rd season of The Bachelor in 2019. Starring a 26-year-old Underwood, Cassie gained national popularity through the show as she was the winner of the season. A native of Orange County, California, Cassie was born on the 27th of April 1995 to Matt Randolph and Amy McCleary. She is the oldest of her parents’ three children and schooled at Berean Christian High School in Walnut Creek, California. She would later attend Biola University in La Mirada, also in California where she obtained a degree in Communication Sciences and Disorders; this was in 2016.

While she is known as a television personality, Cassie is a speech pathologist and is currently pursuing a master’s degree in the field from the University of Wisconsin-Eau Claire. Her career began in 2016 when she was featured in the web series, Young Once.

It is through this web series that people got to known that Colton isn’t the first boyfriend of Cassie; that she dated a professional basketball player named Caelan Tiongson for five years before she meet the former NFL player. People started seeing Cassie as a frontrunner of the 23rd season of The Bachelor right from the beginning of the show, the connection between her and Colton was undeniable. They began a romance that was followed onscreen by anyone who wanted to but Cassie became skeptical about getting engaged to Colton if she emerged the winner; so she broke up with him and decided to quit the show.

Colton also attempted to leave the show but they both returned and resumed dating after Colton disclosed that he wouldn’t propose. He broke up with other finalists of the show and Cassie Randolph officially became the only woman in his life. They went about touring the world and teasing marriage until it emerged in May 2020 that they have parted ways.

What was believed to be an amicable breakup turned messy and they soon unfollowed each other online. By September 2020, it emerged that Cassie filed a restraining order against Colton which was granted. Among other things, she claims he planted a tracking device in her car and had been stalking and harassing her. They later privately settled their differences with the restraining order dropped in November 2020.

2. Becca Kufrin (2018)

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Rebecca Jill Kufrin was born on the 3rd of April 1990 to Jill and Steve Kufrin in Benson, Minnesota. After she graduated from Prior Lake High School, she moved on to Minnesota State University, Mankato, and graduated in 2012 with a degree in Mass Communication. She would then work for Skyya Communications in Minneapolis, Minnesota before she became famous as a contestant on Arie Luyendyk Jr.’s season of The Bachelor.

The dramatic end of the finale which saw Luyendyk who had proclaimed her the winner dump her for the runner-up, Lauren Burnham, earned Kufrin a lot of attention. It was only natural for the show to have her as a lead, this came to pass in the 14th season of The Bachelorette and it was on the show that she met Colton Underwood.

Underwood had to compete for Kufrin’s love on the show and he made quite an impression on Becca as he was one of her final four suitors. But after Becca met the families of the final four suitors, she decided to break up with Underwood. However, they remain friends and speaks fondly of each other.

3. Tia Booth (2017 – 2018)

Tia Booth, like most of the women on this list, is also an American reality television personality. The Weiner, Arkansas native was born on the 11th of August 1991 and apart from her appearances on reality TV shows, she is a physical therapist and a social media influencer. She rose to fame after she was featured on the 22nd season of The Bachelor where she was eliminated in week 8 and then the 5th season of Bachelor in Paradise where she was eliminated in week 4. But it wasn’t on the set of the reality show that the two met. As the story goes, they met on Instagram where they chatted about the popular series, Stranger Things.

After a while, they decided to meet in real life and Tia flew to Los Angeles to spend a weekend with Colton. Now Tia happens to be friends with Becca whom Colton professed his love for in the 14th season of The Bachelorette. Even after Becca rejected his love and he reunited with Tia on season 5 of Bachelor in Paradise, their love was simply not meant to be as Colton claimed he couldn’t connect with her as he wanted.

4. Aly Raisman (2016 – 2017)

Aly Raisman is one of the first popular women that Colton Underwood dated. A two-time Olympian, Aly, born on the 25th of May 1994, is a retired American artistic gymnast. Born in Needham, Massachusetts to Lynn and Rick Raisman, Aly is the oldest of her parents’ four children and has represented the United States in multiple international tournaments. She is one of the victims of the disgraced, former Olympic team physician, Larry Nassar. Aly and Colton’s love story began on an interesting note as Colton asked her out through a video that went viral on social media sites.

They began dating and attended several events together to the delight of their fans. But then, it wasn’t a relationship that was meant to last as they broke up about six months later. The former NFL player disclosed that Aly broke up with him after they attended a Sports Illustrated event in New York City. The former artistic gymnast face-timed him to end the relationship. Based on what he said, Aly ended the relationship because she was confused and overwhelmed. Underwood has related several times that the breakup was hard on him. In one instance, he described Aly as his first love and asserted that his experience with her was the worst heartbreak he had endured.

5. Savannah Chrisley (2017)

Savannah Chrisley is famous as one of the children of the popular American businessman, Todd Chrisley. She was born on the 11th of August 1997 in Atlanta, Georgia, and is a bit of an actress. Even though she doesn’t have much of a career in showbiz, she is a prominent figure thereof. Savannah is the brain behind a popular beauty brand called Sassy. For quite a while, it circulated online that Savannah and Colton Underwood were dating; this was after they were seen together several times.

Nothing was ever confirmed until a few years later. Speaking in August 2020 on Reality Steve’s podcast, Underwood admitted that he and Chrisley were together sometime in 2017. The short-lived relationship, according to Colton, started a few weeks after Aly ended their relationship. He said he and Savannah started talking over social media and he eventually flew out to attend the Academy of Country Music Awards with the Chrisley Knows Best reality TV star. They kept the relationship away from the limelight because he wanted it that way: he had just ended a serious relationship and didn’t want people to be all over his private life.

The Truth About Colton Underwood’s Sexuality

For someone who competed for the love of a woman on a TV show, and had several women compete for his love on another, it is not hard to see why some people have been wondering if the TV star is truly gay. As discussed earlier, Colton Underwood came out of the closet in April 2021 to the surprise of many. In an interview with Robin Roberts on “Good Morning America”, the TV star divulged that he has always been attracted to men but has been running away from who he is all his life for reasons that are not far-fetched. Colton said he never intended to come out but was being blackmailed.

Colton shared that he had secretly visited a spa that’s known to cater to gay people. After he left the venue, he received a message from an anonymous email that claimed to have his nude photos taken at the spa. Whoever was behind the message threatened to out Colton who was left with no option but to forward the message to his publicist, Alex Spieller. At the end of the day, they decided that it was only right for Underwood to embrace his true sexual identity and let the public know about it on his terms.

When The Bachelor star shared his story, a lot of people rallied around to support him for coming out but it was expressed in some quarters that the timing was a ploy to deviate attention from the fact that he was abusive towards his last girlfriend, Cassie Randolph. Colton’s coming out coincided with reports that he would be filming a reality show about his life for Netflix. Some people were not happy about this and have gone as far as setting up a petition on to stop it. The petition, which has gathered over 35 signatures as of September 2021, wants the Netflix documentary to be canceled. It argues that Colton Underwood does not deserve and should not be given a platform.

Chinedu Ndubueze
Chinedu Ndubueze
Chinedu holds a B.SC in Mass Communications with several years of writing and editing experience. He is an advocate of closed-back headphones, horror movies, and dark humor; He believes that Peter Griffin and Stan Smith should be real people. Outside of having to write, edit, and work on other forms of content, Chinedu may keep up with the EPL or listen to everything Eminem and Jon Bellion.


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