Colton Underwood’s run on The Bachelor started as a big “virgin Bachelor” love story and ended up turning into one of the franchise’s messiest, most‑talked‑about arcs, both on and off the show.

Quick Scoop: On the show

Here’s the short version of what happened with Colton on The Bachelor (Season 23):

  • He was cast as the lead and heavily marketed around his virginity storyline.
  • During the final stretch, frontrunner Cassie Randolph decided to leave because she wasn’t sure she could get engaged.
  • Colton had an intense emotional breakdown, jumped a fence, and briefly disappeared from production – the now‑iconic “fence jump” moment.
  • After that, he sent the remaining two women home and pursued Cassie only, ultimately ending the show in a relationship with her but without a proposal.

That “fence jump to chase Cassie” is basically the defining Bachelor moment people remember when they ask what happened with Colton.

After the show: breakup and legal drama

Things got much darker after the fairy‑tale ending:

  • Colton and Cassie dated for a while post‑show, then publicly announced their breakup a little over a year after the finale aired.
  • In September 2020, Cassie filed for a temporary restraining order against him, alleging he sent her harassing messages, showed up uninvited at her home, and even put a tracking device on her car.
  • The order was later dropped after the two reached a private agreement, and they did not continue a relationship or close friendship afterward.

These stalking and harassment allegations made fans and commentators question how the franchise vets its leads and whether red flags were missed when he was cast.

Colton coming out and public reaction

In 2021, Colton came out publicly as gay in an interview and later in a Netflix docuseries about his life.

  • He apologized for his behavior toward Cassie and said he’d been in a dark place while struggling with his identity, but stressed that coming out was not meant to erase or excuse his past actions.
  • Reactions were mixed: some were glad he was living more authentically; others were upset that a man accused of harassment was being rewarded with a new platform and celebratory media coverage.

Since then, he’s continued doing reality TV (including The Traitors), and the Cassie situation still gets brought up whenever people revisit “what really happened” with Colton from The Bachelor days.

TL;DR: On The Bachelor , Colton chased Cassie, jumped the fence, dumped the other finalists, and ended in a non‑engagement relationship with her. After the show, they broke up, she obtained and then dropped a restraining order alleging stalking and harassment, and he later came out as gay and publicly apologized, while ongoing debate continues about his behavior and how the franchise handled it.

Information gathered from public forums or data available on the internet and portrayed here.