The Bachelor season rankings: All Bachelor seasons ranked

7. Colton Underwood: Season 23

If you’ve recently stumbled across Bachelor Nation and its riveting shows, it’s likely your first season was that of Colton Underwood. It’s a strange occurrence but for some reason, many folks started watching from his season onwards. And what an interesting starting point to have, right?

Colton started his Bachelor Nation journey as a contestant on Becca Kufrin’s season of The Bachelorette but was sent home around week 8. He gave love another shot during the fifth season of Bachelor in Paradise, but once again Cupid was not entirely on his side.

However, he did get another chance when he became the lead for the 23rd season of The Bachelor where his virginity was on full display and a topic of discussion the entire time. There’s a lot one can discuss when it comes to Colton’s season, but most notably are the group of women who competed on there. A lot of them went on to become fan favorites including Demi Burnett and Hannah Godwin, and two even became the Bachelorettes, Tayshia Adams, and Hannah Brown.

Along with the outstanding group of girls, there is one part of Colton’s season that we won’t soon forget–the fence jump seen around the world. During the course of his season, it was very clear that Colton had his heart set on Cassie Randolph. However, she had her reservations about leaving the show engaged and chose to break up with Colton before the season ended.

In complete and total frustration and heartbreak, Colton ran away from the cameras and jumped over a fence to get as far away from the situation as possible. Despite Chris Harrison and the crew attempting to run after him, he was deadset on escaping what had just happened.

Cassie may have broken up with Colton, but the couple worked things out during the season finale (I can’t relive the scene during which he breaks up with Hannah G. ever again) and decided to date instead of getting engaged. And date they did for a little over a year until things grew tense between the couple and they decided to call it quits earlier this year.

Their breakup was very publicized and allegedly resulted in Cassie getting a restraining order against him, although that has never been confirmed. It’s tough to say what went wrong since the days of Colton jumping over the fence for Cassie, but as of now, it looks like Colton is still on the market to find himself a wife.