Kaitlyn Bristowe, Nick Viall’s Messy Relationship Timeline

Not all Bachelor Nation breakups are created equal. Years after Kaitlyn Bristowe and Nick Viall’s controversial relationship played out on season 11 of The Bachelorette, the exes struggled to stay on good terms.

Following Nick’s stint on season 10 of The Bachelorette, in which he was the runner-up for Andi Dorfman’s heart, he started talking to Kaitlyn, who attempted to find love with Chris Soules on season 19 of The Bachelor. The Natural Habits creator dished on their pre-show relationship on a January 2019 episode of his “Viall Files” podcast, admitting they talked “every day, all day,” on the phone and via FaceTime.

After striking up a relationship, however, Kaitlyn was offered the chance to be the Bachelorette for season 11. Still interested in pursuing a future with the former dance teacher, Nick crashed a group date on her season and joined the cast. Despite the romantic gesture — and pre-fantasy suite hookup — Kaitlyn found herself falling for fellow contestant Shawn Booth and rejected Nick mid-proposal during the finale.

“It was more personal because of the relationship before and all the things that happened leading up to it,” Nick admitted on his podcast in January 2019. “Everyone knows at this point that Kaitlyn and I had chatted before. I haven’t shied away from that.”

“At that point, she was just kind of a friend and we were kind of going down that path of flirting and talking ridiculous things and then that kind of snowballed when she went on [Jimmy] Kimmel,” he continued. “I remember her texting me and saying, ‘Hey, make sure you watch.’ She was like, ‘I’ll throw you signals. I’m going to keep touching my lip with my fingers.’ She did that!”

Nick and Kaitlyn’s post-show relationship has faced several ups and downs following their split, including the “Off the Vine” podcast host accusing her ex of not joining the franchise for the right reasons.

Scroll through for a complete timeline of Nick and Kaitlyn’s relationship:

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