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Colton Underwood and Cassie Randolph's Relationship Timeline

A Bachelor Nation love story. Colton Underwood and Cassie Randolph didn’t have the traditional romance — or even the traditional Bachelor timeline. However, from the moment they met on the season 23 Bachelor premiere, the pair were connected.

Although their onscreen journey wasn’t an easy one (the fence jump!), they began a real relationship after the cameras stopped.

“It was a lot of changes, for sure, because we went from these more simple, more normal lives and then all of a sudden, we film a show and then you’re thrown into craziness where everyone is very hyperaware of everything that goes on in your life and your relationship,” the speech pathologist told Us Weekly exclusively in October 2019. “It was a little bit of a struggle at first, I think — like adjusting to everything. But I feel like now we’ve kind of gotten used to it and learned to balance everything a lot more.”

The former NFL player also noted that the show actually helped them grow their relationship.

“I think you learn to communicate too,” he explained. “Just with whether it’s tabloids or someone speculating a certain thing or people reading into your body language, you know. You just learn how to communicate with each other and you’ll be on the same page with everything going on. … Nobody could ever prepare you for what life is like after that. Like, you can have people tell you all you want, like, ‘Oh, wait for this, wait for this.’ But until you’re in it, you don’t really get the full magnitude of it.”

Colton later revealed that while he got a great outcome, he felt a bit “burnt” by the shows’ producers.

“They always asked to rank the girls. And very early on, Hannah [Godwin] was up there. And she got left off of a date,” he said in August 2019. “I sort of recall remember feeling a little burnt when they did that. I was like, ‘So let me get this straight. Hannah’s No. 1 on my list right now, and she’s not getting a date this week?’”

He then decided to change things: “From there on out, I was like, ‘All right, if you’re going to do that to my top girls, I’m not really going to tell you who my top girls are, because I don’t want you messing with them.’ So in a weird way, I tried to defend myself and defend the girls by not being truthful to them who my top was.”

Scroll through the gallery below for a full timeline of Colton and Cassie’s relationship.

strong>Listen on Spotify to Here For the Right Reasons to get inside scoop about the Bachelor franchise and exclusive interviews from contestants.
January 2019

During the premiere, Colton and Cassie met in front of the mansion and she brought a box of butterflies.“I have so many butterflies. Literally, I have so many butterflies," she said and he put one in his jacket pocket.

ABC/Rick Rowel
January 2019

During week 4 of The Bachelor, the group went to Singapore and got their fortunes read. The woman told Cassie she was Colton’s sister in a past life!

ABC/Rick Rowel
February 2019

During a one-on-one date in Thailand, the pair went on a boat ride together. They had many important conversations and after dinner, they crawled in bed together to cuddle and he told her he was crazy about her.

ABC
February 2019

During hometown dates, Colton met Cassie's family. Cassie's dad was very skeptical of Colton. In fact, he was the only one who didn't give Colton his blessing to propose to Cassie. She also wasn't sure how she felt and he was worried after she didn't drop the L-word.

ABC/Rick Rowel
March 2019

During week nine, her dad returned to have a talk with Cassie about her future with Colton. She was extremely torn and told Colton she loved him but isn't ready to be engaged. He said that she's The One, but she wasn't sure she can move on — she loved him but isn't fully in love. In turn, she chose to leave. Colton was so upset that he jumped over a fence and tried to leave the show.

ABC
March 2019

During the finale, Colton ended things with the other women and went to Cassie's hotel room to tell her she's the only one left. She decided to give their relationship a chance. During the live aftershow, Colton revealed he moved to Los Angeles to live closer to Cassie.

ABC/John Fleenor
March 2019

Less than two weeks later, the couple traveled to Las Vegas and Cassie wore a jacket that read "Future Mrs. Underwood" on the back.

Courtesy of Vegas Golden Knights
May 2019

A few months later, the pair revealed exclusively to Us that they were not going to "rush" into an engagement or moving in together. "We really don’t have a timeline," she said at the time. “We’ve definitely talked about it, but we’re just enjoying right now and not worrying about it.”

Jeff Christensen
June 2019

The couple traveled to Bermuda over the summer and shared multiple PDA-filled pics from their trip.

Courtesy of Cassie Randolph/Instagram
August 2019

In Colton's book, The First Time, he revealed that he and Cassie briefly split over the summer. However, it only lasted a few days as he missed her too much.

Shutterstock
November 2019

The couple celebrated their first anniversary in November, heading to St. Lucia together.

"One year ago today they put the cameras down and we cooked our first meal together in Mallorca, Spain. I knew then that loving you was going to be easy, but I couldn’t have imagined this. You have shown me the power of love and I never knew that I could love like this," he wrote on Instagram at the time. "Thank you for making me the happiest man alive. I love all of you Cass."

Courtesy of Colton Underwood/Instagram
March 2020

When Colton tested positive for coronavirus, he became quarantined at Cassie's home and she took care of him until he felt better.

Courtesy of Cassie Randolph/Instagram


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