Nick Viall’s Dating History: Looking Back at the Former Bachelor’s Love Life

Credit: ABC (5)

Nick Viall's Dating History: Looking Back at the Former Bachelor's Love Life

Once a Bachelor, always a Bachelor? Nick Viall made his franchise debut in 2014 on season 10 of The Bachelorette — and it turned out that it was his first of many appearances. After coming in second on Andi Dorfman's season, he returned for season 11 and joined Katilyn Bristowe's season. He then tried to find love on season 3 of Bachelor in Paradise — and when those didn't work, he became the Bachelor. "A lot of people have this perception that doing it four times is a failure," he told Glamour in 2017. "It’s not a competition, but I look at it like this: Look at Andi and Kaitlyn. I connected with two women that, in reality, I realize I wasn’t their type, but I was able to build very strong connections with both women. It didn’t work out and probably for the best, but there were also 24 men who went home before I did on both of those seasons. So, there were a lot of great things about those relationships. Ultimately they didn’t work out because I don’t think they were supposed to work out. I don’t think it was something that I did wrong. I don’t think if I would have done anything different that those relationships then would have worked out." [jwplayer ul5DIQBm] From the start, the Wisconsin native had a bit of a villain vibe. After being blindsided by Dorfman on the finale, he revealed on the live After the Final Rose special that the two had slept together in the fantasy suite. During Bristowe's season, he became even more known for his sex-positive attitude when the pair slept together earlier in the season during their date in Ireland. However, he's not ashamed of that. "Kaitlyn showed a lot of courage by admitting 2 having sex on national TV knowing that she will be unfairly judged by some. Both men and women have an equal right to have sex without judgment," he shared via Twitter in 2012. "Not sure why we still have double standards about sex when it comes to men and women. Dating can be tough to navigate especially in unique situations. The fact that Kaitlyn acknowledges that there are others involved in this situation that could be affected by her decision shows she respects the emotional connection men can have to sex." Scroll through the gallery below for all of Viall's relationships through the years. [podcast_block]

Credit: ABC (5)

Nick Viall's Dating History: Looking Back at the Former Bachelor's Love Life

Once a Bachelor, always a Bachelor? Nick Viall made his franchise debut in 2014 on season 10 of The Bachelorette — and it turned out that it was his first of many appearances. After coming in second on Andi Dorfman's season, he returned for season 11 and joined Katilyn Bristowe's season. He then tried to find love on season 3 of Bachelor in Paradise — and when those didn't work, he became the Bachelor. "A lot of people have this perception that doing it four times is a failure," he told Glamour in 2017. "It’s not a competition, but I look at it like this: Look at Andi and Kaitlyn. I connected with two women that, in reality, I realize I wasn’t their type, but I was able to build very strong connections with both women. It didn’t work out and probably for the best, but there were also 24 men who went home before I did on both of those seasons. So, there were a lot of great things about those relationships. Ultimately they didn’t work out because I don’t think they were supposed to work out. I don’t think it was something that I did wrong. I don’t think if I would have done anything different that those relationships then would have worked out." [jwplayer ul5DIQBm] From the start, the Wisconsin native had a bit of a villain vibe. After being blindsided by Dorfman on the finale, he revealed on the live After the Final Rose special that the two had slept together in the fantasy suite. During Bristowe's season, he became even more known for his sex-positive attitude when the pair slept together earlier in the season during their date in Ireland. However, he's not ashamed of that. "Kaitlyn showed a lot of courage by admitting 2 having sex on national TV knowing that she will be unfairly judged by some. Both men and women have an equal right to have sex without judgment," he shared via Twitter in 2012. "Not sure why we still have double standards about sex when it comes to men and women. Dating can be tough to navigate especially in unique situations. The fact that Kaitlyn acknowledges that there are others involved in this situation that could be affected by her decision shows she respects the emotional connection men can have to sex." Scroll through the gallery below for all of Viall's relationships through the years. [podcast_block]

Credit: Courtesy of Nick Viall/Instagram

Natalie Joy

Viall was initially first linked to Natalie Joy in 2019, but the couple kept their romance quiet. They became Instagram official in December 2020 when Joy shared an Instagram video of them playing a virtual reality game and she tried to give him a kiss.

A source exclusively told Us that the pair's relationship is "very real."

“They’ve been dating since the beginning of COVID but have just started going public. They’re pretty much inseparable. You can say she practically lives with him because she’s at his house that much," the insider revealed in February 2021.

Credit: ABC/Barbara Zanon

Andi Dorfman

Although the two never dated outside of the show, Dorfman and Viall shared a real connection during season 10, his first season, of The Bachelorette. She ultimately chose Josh Murray at the end, but stayed friends with Viall — even later popping up to give him advice during his season of The Bachelor.

"We’ll like talk here and there, every once in a while,” Dorfman told Us in January 2018. “You know, like check in with each other. But that’s about it. No [hard feelings].”

Credit: ABC/Rick Rowell

Kaitlyn Bristowe

In 2015, Viall showed up during the fourth week of season 11 of The Bachelorette, asking Bristowe to give him a chance. She agreed and he joined the season. He later revealed that the duo talked “every day, all day,” on the phone and via FaceTime before she began filming.

“It was more personal because of the relationship before and all the things that happened leading up to it,” he said on the "Viall Files" podcast in January 2019. “Everyone knows at this point that Kaitlyn and I had chatted before. I haven’t shied away from that."

The two slept together two weeks after he joined the cast, but ultimately, she chose Shawn Booth over him when it came time for the finale, stopping Viall moments before he proposed. During the live after show, Viall claimed the two had exchanged "I love you's" so he was completely shocked by her choice.

Credit: ABC/Rick Rowell

Leah Block

When Viall arrived in Mexico for Bachelor in Paradise, Leah Block was the first to ask him on a date. While the two connected and shared a kiss by the ocean, he was given another date card later that night and quickly moved on to Amanda Stanton.

Credit: ABC/Rick Rowell

Amanda Stanton

Stanton and Viall connected from the moment they met on Paradise and shared a very steamy makeout next to a bonfire on the beach. However, when Josh Murray — the man Viall had lost to on Dorfman's season — arrived the next day, he asked her out. She chose to continue the journey with Murray. (The two got engaged in the end but broke it off in 2016.)

Credit: ABC/Rick Rowell/

Jen Saviano

It took Viall a bit of time but during week 3, Jen Saviano entered Paradise and connected with the Bachelorette alum. The pair begin dating and make it to finale with him even choosing an engagement ring. She tells him how much she loves him but ultimately, he said he wasn't 100 percent sure. "I wanted to say I was in love with you, but something in my heart just said I can't," he told her and they both left heartbroken.

Credit: ABC/Phillippe Bosse; ABC/Terhi Tuovinen (inset)

Vanessa Grimaldi

In August 2016, Viall became the Bachelor and fell in love with Vanessa Grimaldi. Instead of 25 women, his season included 30 women. He proposed to Grimaldi, a special education teacher from Canada in the season finale. The pair split in August 2017 after a nine-month engagement. "There’s a lot of mutual respect,” he told Us in 2018. “We don’t actively keep in touch but I’m sure we’d be there for each other if need be. We have a lot of other things going on in our lives. We are leading separate lives, of course."