Colton Underwood’s Girlfriend 2020: Who Is Colton Dating?

Colton Underwood is a former NFL player and American television personality. In 2014, he was signed as a free agent by the San Diego Chargers and was on the practice squad of the Oakland Raiders and the Philadelphia Eagles. About a year after being released by the Raiders, Underwood became a contestant on the 14th season of The Bachelorette and was eliminated after the eighth week. A little after The Bachelorette, Underwood was cast in the fifth season of Bachelor in Paradise. But after being linked to a fellow contestant he left the show during the fourth week. After his time on Bachelor in Paradise, ABC announced that Underwood would be the lead in the 23rd season of The Bachelor.
Since his time on reality television, Underwood was not very lucky when it came to love even if he tried to make it work. Now, it seems like he has moved on in his dating life very quickly.

Becca Kufrin

Underwood was a contestant on The Bachelorette in 2018 where he was one of the 25 men vying for Becca Kufrin’s heart. During that season, he was a frontrunner and a fan favorite among Bachelor Nation. He ended up not getting a rose after the hometown dates and was sent home. His relationship with Kufrin was very short-lived.

Cassie Randolph

Cassie Randolph

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During his time on The Bachelor Underwood met Cassie Randolph, a speech pathology student from Huntington Beach, CA. She ended up leaving on her own during the final three after revealing to Underwood that she did not want to be engaged at the end of the competition. After she left, it caused Underwood’s iconic “fence jump” which was talked about the next day on all media platforms. In the following episode, Randolph returned after Underwood revealed that he wanted to be with her and promised that he would not propose. He also revealed that he sent the other two finalists home after realizing his true feelings. At the After the Final Rose special, both Underwood and Randolph revealed that they were a couple.
After two years of dating, Underwood and Randolph ended their relationship back in May. In an interview with Chris Harrison during The Bachelor: The Greatest Seasons Ever, Randolph revealed that neither her nor Underwood have fully explained what caused the break-up and are not ready to go into detail.
“It’s been really hard, and I think going through any break-up is really hard, but then going through one in public comes with a whole new set of challenges,” said Randolph. “So we’re both kind of learning to navigate it; we’re on good terms and we’re hanging in there.”

Lucy Hale


Two months after his breakup, Underwood has been casually dating actress Lucy Hale. TMZ posted a photo of him out on a hike with the Pretty Little Liars star and they have been “seeing each other a lot” over the past few weeks. As of now, neither Underwood nor Hale has made a public comment about where their relationship stands.

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