Jason, who met Kaitlyn while taping an episode of her podcast in October 2018 and took her out on their first date in January 2019, admitted timing is everything and popping the question on TV following a three-hour recap of Kaitlyn's The Bachelorette season simply wasn't the right time.
"The whole backstory -- spilling a little tea here -- they actually came to me asking me if I'd like to take this opportunity to propose," Jason toldEntertainment Tonight of show producers.
"After thinking through it, in no form was there any pressure. They were just like, 'Hey, if you think this is the right time, we're here to support it, we'll take care of it and make it special.'"
Jason revealed he "didn't even bring it up to Kaitlyn" and made the decision on his own.
"I shot it down after about a day of thinking because I'm just like, 'Listen, this is a part of her history and a part of our story, [but for] what's next, we don't need these stories to align in the same showing," Jason explained.
After all, The Bachelor: The Greatest Seasons -- Ever! showed Kaitlyn making out with men, sleeping with Nick Viall, crying over broken hearts, and getting engaged to another man, Shawn Booth, from whom Kaitlyn split in November 2018.
"So I shot it down, but I told Kaitlyn after [I shared my decision]. I said, 'Hey, I want to let you know that they came to me and I did decline it,' Jason shared.
"And she was like, 'Thank God! I wouldn't want [our engagement] to be then either.' So we were on the same page."
Jason said he and Kaitlyn had this talk before videochatting with host Chris Harrison on The Bachelor: The Greatest Seasons -- Ever!; however, Kaitlyn still got freaked out when Harrison said he had "a surprise" for her and then she felt a box in Jason's pocket.
"It just shocked me for a second," Kaitlyn shared, thinking Jason's Airpods could have been a ring box in that moment.
"Then [Harrison] says, 'Do you want to go on Dancing With the Stars?'" Kaitlyn recalled. "Jason and I looked at each other. I could not speak."
"We were sitting outside by the fire the other night just having a glass of wine, and we had such a good day, and I remember him just being like, 'Should we look at rings?' And I was like, 'Okay!' -- which we've done a couple times," Kaitlyn said.
But Kaitlyn admitted he wouldn't be interested in "a quarantine proposal."
"I don't want one," Kaitlyn noted. "All I know is that I don't want it to be like, live somehow in front of people. I want it to be a private moment. I don't want it to be quarantined, but I want it to be private."
Kaitlyn's former relationship with Shawn lasted for over three years, but she quickly moved on with Jason in 2019.
After going on their first date, Kaitlyn said she decided to take Jason -- who admittedly had a crush on her right after meeting the previous year -- out of the friend zone.