The 35-year-old The Bachelorette Season 11 alum and the 32-year-old banker confirmed that they were engaged on social media in May.
In an appearance on the Click Bait with Bachelor Nation podcast on Thursday (July 16), Jason opened up about his proposal and shared some of the obstacles he ran into leading up to the moment he popped the question.
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Jason said that he “knew a while ago” that he wanted to marry Kaitlyn and he put a lot of thought into planning the perfect proposal.
“The problem is is there’s so many moving parts in our lives right now,” he explained. “And to me, the biggest part of the engagement, no matter what, wasn’t the thrills or the money or any of this stuff behind like, what I would do. It’s more about, literally, her friends and family.”
He continued, “So, for so long, [we’re going], ‘How can we figure this out? How can we get her family?’ Then, I have a plan. Then, COVID hits. Then, [it’s like] what the hell are we going to do, right? Then the summer of 2020, if you remember, kind of COVID pulled back a little bit. So I thought we had a good plan in place and then boom, Dancing with the Stars hit and then Kaitlyn‘s in Canada [and it] totally shut down. So the planning process was an absolute nightmare of trying to figure out what I could do, but then it got to a point like, you can’t let the uncontrollables control your entire life. So [I] just had to make something work.”
Jason then decided to propose during a trip to visit Kaitlyn‘s parents in Mexico this last spring and he was “inches” away from pulling it off before he encountered another problem.
“I ran into all these border issues actually bringing the ring over,” he said. “So I had to detour the whole plan, because I was going to do it in Mexico with her mom and [I] had this whole setup. I realized I couldn’t bring this over. If I bring it over as like, my asset, it’s considered an asset of mine. At the value of what the ring is, I would have to totally disclose it and then show receipts. And I’m traveling with Kaitlyn, so how could I? And if I did do that and it got sniped, it would have been a whole production.”
Jason recalled “scrambling” to figure out a new plan and started “venting” to his mother, who ended up helping him get things back on track.
“My mom, actually, was a big part of helping me come up with the creative [aspect of the proposal],” he shared. “She was like, ‘You know, you guys met on the podcast.’ I was like, ‘Ah!’ So I proposed to her on the podcast. She had no idea!”
Kaitlyn and Jason first met in October 2018 when he appeared on her podcast Off the Vine. They then confirmed they were dating in January 2019 before moving in together in Nashville.
Kaitlyn recently clapped back at trolls for criticizing her “different” appearance.