Meet Colton Underwood’s Ex-Girlfriends: Before and After ‘The Bachelor’

When it comes to love, Colton Underwood is a hopeless romantic — his dating history on and off The Bachelor proves it. His most recent relationship was with Cassie Randolph, whom he seemed to be head over heels for. Unfortunately, the two didn’t last.

Since the very beginning, Colton had a soft spot for Cassie, who appeared on season 23 of the show. However, at the time, Cassie was not ready to go all the way with Colton and as a result, ended up eliminating herself. “Today was perfect, and I love you so much,” she said at the time. “After today, I’m not like, in love. I don’t know why after today, I’m not … I feel like I’m having doubts about it.”

After Cassie left, Colton went after her “asking for a second chance to take it day by day and figure it out.” It worked out in his favor because the pair went on to date for nearly two years before their split in May 2020.

Colton was so in love with Cassie, he revealed to fans via Instagram that he was planning on popping the question sometime in 2020. “Proposal coming in 2020????” a fan commented on a sweet post he dedicated to his beau. “Probably,” he responded to the follower.

Unfortunately, the couple never got engaged, but they are still amicable. “It’s been a crazy few months, to say the least, Cass and I have been doing a lot of self-reflecting,” he wrote, announcing their breakup. “Sometimes people are just meant to be friends — and that’s OK. We both have grown immensely and been through so much together — so this isn’t the end of our story, it’s the start of a whole new chapter for us.”

Cassie also shared a message with fans about their split. “Colton and I have broken up, but have decided to remain a part of each other’s lives,” she wrote. “With all that we have gone through, we have a special bond that will always be there. I love Colton very much and have an enormous amount of respect for him.”

Keep scrolling to learn more about Colton’s dating history.