Viewers first met the Seattle resident on season 4 of The Bachelorette. After DeAnna Pappas turned down his proposal, Jason, a single father at the time, was named the 13th Bachelor. While Jason found love and proposed to Melissa Rycroft during the 2009 finale, he later changed his mind and revealed he wanted to pursue a relationship with runner-up Molly Malaney.
Jason broke the news to Melissa during the After the Final Rose special, which was taped with no audience six weeks after their proposal.
“I didn’t watch it the first time around. And now it’s been what, 11 years? I don’t really need to go back because it’s so far away,” Melissa told Us Weekly in January 2020 after season 13 started streaming on Netflix. “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 makeup. … I mean, it’s just an embarrassing time that was documented that people are getting to relive it again.”
Molly, meanwhile, agreed to give Jason another chance after he officially broke things off with Melissa. After 10 months of dating, he proposed in October 2009.
“I tell this to everyone who asks, ‘What have you learned? What’s the biggest piece of advice you would give people?’ It’s to not care what other people think. If I would’ve listened to what everyone around me was saying after the show, I wouldn’t have stayed with Jason, and we’ve been married for 10 years,” Molly explained Rachel Lindsay and Becca Kufrin on their “Bachelor Happy Hour” podcast in July 2020. “It’s no fun to live life the way other people want you to live your life. You can’t be authentic to yourself then. You’ve got to not care what other people think and just block out the noise.”
ABC revisited season 13 in August 2020 as part of The Bachelor: The Greatest Seasons Ever. Melissa took to Instagram the night before the special aired to reflect on the show.
“Considering what is about to air tomorrow, let me just say: I am SOOO glad that it happened – all of it!” she wrote alongside a photo with husband Tye. “I wouldn’t be with this guy, I wouldn’t have my babies, I wouldn’t have my career, and I wouldn’t be who I am today if it hadn’t happened – even the way it happened. It was totally embarrassing but totally worth it ☺️.”
Scroll through for an update on the biggest names from Jason’s season: