During the first episode of his new podcast, The Viall Files, the former Bachelor star revealed what his relationship with Bristowe, 33, was like before their time together on her season of The Bachelorette, how they managed to get away with secret calls and meetings, and whether or not he still has feelings for her.
Accompanied by actress and friend Ashley (Hinshaw) Grace, the duo kicked off the conversation by discussing breakups. After Grace asked Viall which breakup was harder — his split from season 10 Bachelorette Andi Dorfman or Bristowe — the reality TV star had a lot to say.
“They were very different,” said Viall, 38. “The one that was more personal was Kaitlyn. … It was more personal because of the relationship before and all the things that happened leading up to it.”
“Everyone knows at this point that Kaitlyn and I had chatted before,” he added. “I haven’t shied away from that.”
Inquiring about a storyline on the 19th season of The Bachelor (with Chris Soules), which Bristowe appeared on, Viall said he messaged her on Twitter and “that’s how the seal was broken.” Before he knew it, they were talking “every day, all day.”
After sparking up a flirty relationship via phone and FaceTime, Bristowe was asked to be in the running for the next Bachelorette.
“I remember when she found out [that there was going to be two Bachelorettes on her season] she was really upset,” Viall, who recently launched an essential oil line called Natural Habits, recalled. “At that point, she was just kind of a friend and we were kind of going down that path of flirting and talking ridiculous things, and then that kind of snowballed when she went on [Jimmy] Kimmel. I remember her texting me and saying, ‘Hey make sure you watch.’ She was like, ‘I’ll throw you signals. I’m going to keep touching my lip with my fingers.’ She did that!”
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He added, “At that point, she was filming her packages and was like, ‘Oh my god, they’re taking my phone away. That night she snuck and called me from her hotel room and we had our goodbye conversation. We were both like, ‘I feel like saying something crazy but I’m not going to say it.’ It was this puppy love thing. The big X factor was, there’s two Bachelorettes. I remember saying to her, ‘I’m going to be honest I hope you don’t get picked.’ The thought was, if you don’t get picked you’re going to fly to Chicago and come visit me. It was a conversation.”
After the contestants voted for Bristowe as the next Bachelorette over Britt Nilsson, Viall said he was bummed but open to the idea of coming on her season — something he and Bristowe had previously talked about.
As producers tried to recruit him to appear on Bachelor in Paradise, Viall recalled being hesitant and telling them, “Too bad Kaitlyn is your Bachelorette, because then it would’ve been different.”
“I just kind of said that for fun,” he said. “The next day I got a call from a higher up and they were like, ‘Do you want to meet her?”
“I was following the season like a crazy fan (via Reality Steve) with no anticipation of coming back on,” he said. “And then from the time the producer called me and said do you want to meet her, I was in New York two days later.”
When Viall arrived in New York, he tried to keep an open mind.
“I was pretty confident that she would keep me on but prepared myself that she might not,” he said.
Viall received a message on Twitter early that morning from Bristowe that read, “It’s Kaitlyn, call me. Here’s the number.”
While Viall was convinced she knew he was in New York, she actually had no idea.
“She’s talking to me and she’s like, ‘It’s going really well, and the guys are really nice but, like, I miss you and I feel like it’s different from we had.'”
“We talked all night long,” he adds. “She was like, ‘Just come.’ And I said, ‘Well what would you do if I come?’ She said, ‘Ill just fake it with the rest.’ She did say, ‘There is this one guy. I do like him. I have this connection to him.’ Come to realize that was Shawn [Booth] at the time.”
Viall says he has previously declined to open up about this in years past because Bristowe was happily engaged to Booth. However, the couple, who were together for three years, split in November.
After Viall’s surprise return on The Bachelorette, Bristowe called him that night and asked him to come to her hotel, he said.
“I put this hoodie on, snuck into her room and we were hanging out all night,” he says. “It was a lot of fun. We did not have sex.”
While Viall ended up being heartbroken in the end, he said it was for the best.
“She did me a huge favor in picking Shawn,” he said. “They clearly were a good match. They didn’t work out. They dated for three years. I don’t think Kaitlyn and I would’ve ever come close to that.”
Viall, who went on to become the Bachelorin 2016, said his experience with Bristowe was a lesson learned.
“My biggest takeaway in my story with Kaitlyn, sometimes people say things in the moment, and we shouldn’t get caught up in those moments,” he said.