Bachelor Nation's Dean Unglert, Caelynn Miller-Keyes’ Relationship Timeline

Dean Unglert and Caelynn Miller-Keyes have been dubbed a Bachelor success story, but their relationship got off to a rocky start.

Unglert returned to Bachelor in Paradise for season 6 during the summer of 2019 after he found himself in the middle of a messy love triangle on season 5. During his second stint on the beach, he met Miller-Keyes, who was the one wrapped up in that summer’s drama.

“A long time ago, when we first started dating, there were things where I was, like, disappointed about or just upset to hear, you know what I mean, about Caelynn’s dating history,” Unglert admitted to the former Miss North Carolina on his “Help! I Suck at Dating” podcast in November 2020. “And I was like, ‘Well, dude, if you were to flip it around and put me in the same position that I’m putting her in, I would look 20 times worse.’”

During season 6 of BiP, fans learned Miller-Keyes hooked up with Blake Horstmann at Stagecoach before filming began. She called him out on the show, revealing he slept with her and their costar Kristina Schulman at the music festival. Horstmann subsequently tried to clear his name by sharing his texts with Miller-Keyes.

After a messy summer, Unglert and Miller-Keyes left the beach together — and they’re still going strong. In October 2022, Us Weekly confirmed the duo’s engagement after three years together. They’ve since tied the knot in September 2023.

Scroll through for their timeline: