From the Fence Jump to a Restraining Order: Inside Cassie Randolph and Colton Underwood’s Journey

Ups and downs. Colton Underwood and Cassie Randolph fell in love during season 23 of The Bachelor, but their relationship started off on a rocky note. The contestant eliminated herself because she wasn’t ready to get engaged, but Colton was willing to do anything to prove she was the one for him. After sending his other finalists, Hannah Godwin and Tayshia Adams, home, plus one epic fence jump, the former football player got his girl.

Nearly two years later, the couple announced their split in May 2020, and their breakup got extremely messy after Cassie accused her ex of stalking her and filed a restraining order, which she later dropped. In April 2021, Colton came out as gay during an appearance on Good Morning America.

Despite no longer being an item, the former couple shared many special moments together. So much, in fact, Colton was planning on popping the question. “I promise to still tell bad jokes, forget to clean up after myself, mispronounce easy words and love you with everything I have in this new year,” the former Bachelor captioned an Instagram photo with Cassie in January 2020.

The sweet post prompted a fan to ask, “Proposal coming in 2020????” to which Colton replied, “Probably.”

It turns out, Colton had been thinking about proposing. “I’ve creeped on her Pinterest boards, so I already have an idea,” he shared with Life & Style and other outlets during the 2019 E! People’s Choice Awards in November.

However, the couple split before they ever got engaged. Though the breakup was amicable at first, it was a struggle for them to adjust. The pair of exes have both been vocal about their hardship following their split, especially Cassie, who is had a difficult time dealing with hate from trolls online.

“The last two years, I’ve been thrust into [the] spotlight after living a fairly normal life,” she shared on Instagram in July 2020. “I used to think a platform would give me a voice, but in many ways, a platform takes your voice. For someone like me, it’s been paralyzing. I can overthink everything. It takes really thick skin to navigate constant drama, fake articles, nasty DMs and comments or rumors started by people who feel entitled to your personal life.”

The reality TV couple’s relationship was filled with highs and lows. Keep scrolling to see Colton and Cassie’s relationship timeline.