This wasn’t Viall’s first time making it to the final two on The Bachelorette: He also came in second place while courting Andi Dorfman on the show last spring.
The two-time runner-up sat down with Bristowe on Monday night on After the Final Rose for the first time since she sent him home.
“You know, that day you wake up and you think you have all these reasons to be confident,” said Viall of how he felt going into the proposal day. “I don’t know when you finally knew [that you were sending me home] but you certainly knew when I got out of the limo. And I show up, and I start talking and I pause – and you kind of let me continue.”
“I just felt like those words that I said to you, once you knew, they were no longer meant for you. They were meant for someone that felt the same way that I felt about them,” he added. “That moment I had – those words I said to you – I will never get that back.”
While Viall said he knows that Bristowe didn’t “mean anything malicious by it,” he was still open about his confusion.
“I just don’t quite understand what the heck you were thinking,” he said. “Like, ‘Well there’s no good way but this is the best way to break his heart’?”
Bristowe said she completely understood where Viall was coming from.
“I did [care for him deeply] and it was excruciating,” said Bristowe. “A part of me thought, should I go to you in the morning? Or will it be just as hard five hours later? I didn t really know. When I look back, I’m like, should I have done it a different way?”
When Viall asked her how she feels now, she acknowledged that she thinks she should have handled the break up differently.
“Yes, I probably should have,” she said. “But at the same time I had so many thoughts going through my head.”
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Clearly still searching for answers, Viall did circle back in their conversation to ask if Bristowe thought allowing him to pick out a ring, think of a proposal speech and go through the whole speech was the best thing to do when she knew she was ultimately going to send him home – but when time began to run out on the live show, Viall made a point to cut himself off and end the talk on a more positive note.
“I do want to wish you the best,” he Viall.
Bristowe thanked him and the two shared a hug.
As for the newly engaged and now former Bachelorette, Bristowe was all smiles and giggles when fiancé Shawn Booth sat back down with her to conclude the show.
“Honestly, we woke up this morning just being like, ‘it’s Christmas!'” exclaimed a giddy Bristowe.
“We honestly just want to start living life,” she continued. “Being around family, being around people that we love, being around that love us.”
For much more from Kaitlyn and Shawn, including exclusive photos, pick up the new issue of PEOPLE, on stands Friday