Jason, a then-single father from Seattle, first appeared on season 4 of The Bachelorette in 2008. While he was ready to get down on one knee during the season finale, DeAnna Pappas rejected him and accepted a proposal from Jesse Csincsak. (The twosome called it quits in November 2008.)
The account executive, who shares son Ty with ex-wife Hilary Buckholz, went on to be named the lead for season 13 of The Bachelor, which premiered in January 2009. While he originally picked Melissa Rycroft to be his wife, Jason changed his mind after proposing. The show then moved up the typically live After the Final Rose taping so Jason could break up with Melissa and tell Molly, the runner-up, he wanted to be with her.
After the drama unfolded onscreen in March 2009, Jason proposed to Molly that October.
“Melissa is a great girl, but there wasn’t any chemistry,” he told Us Weekly at the time. “So I broke up with her after Christmas, about a month after we wrapped. Obviously, I didn’t want it all on TV, but I had to take the chance if it meant getting [Molly] back. I’d rather have picked up the phone, trust me!”
Melissa, for her part, reconnected with boyfriend Tye Strickland after she was dumped by Jason. The twosome, who wed in December 2009, now have three kids. While the former Dallas Cowboys cheerleader is happily married, she opened up about how embarrassing it was to relive the drama when The Bachelor season 13 was added to Netflix in January 2020.
“I don’t really need to go back because it’s so far away,” she told Us. “However, of course, I’m getting sent screenshots, and memes, and stuff that people are now watching and finding. I had, like, the poof in my hair. I was wearing tank tops and scarves, it was a mess. There was no YouTube to show us how to contour, or do makeup. … I mean, it’s just an embarrassing time that was documented that people are getting to relive it again. … Tye watched it the first time around, which was his mistake, so he has those images ingrained in him forever.”
Scroll through to revisit Jason and Molly’s love story: