Olivia Culpo Dating History: Ex-Boyfriends, Relationships

It’s raining men! Olivia Culpo is known for her stunning looks and heavy media presence, but she should also be praised for her impressive dating history, too.

While she doesn’t speak much publicly about her relationships, Olivia is set to reflect on a past relationship in her November 2022 Culpo Sisters reality series.

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“I was with somebody that did really horrible, horrible things,” she shared on the TLC show. “I was made to feel like a less-than-human in every sense of the word. I’ve never talked about it before.”

The 2012 Miss USA winner has dated multiple men in the entertainment industry and sports world, from Nick Jonas to former NFL star Tim Tebow. Nowadays, she’s happily engaged to San Francisco 49ers running back Christian McCaffery.

Keep reading to learn more about Olivia’s dating history!

Ryan Lochte

Olivia and the Olympic gold medalist swimmer sparked relationship rumors in September 2012.

Although she hasn’t spoken out about the athlete, he gushed over the Rhode Island native the same month. “She is beautiful. I love hanging out with her,” he told E! News. “She has a great sense of humor, she makes me laugh, she’s just a good girl to hang out with.”

He even praised her for becoming Miss USA a year into her entering the pageant world.

Nick Jonas

The two were so serious that she thought he was going to pop the big question, especially after he knelt down on one knee to her in the middle of the 2014 Miss Universe pageant.

After they broke up in 2015, Olivia revealed her true feelings in an emotional Instagram post. “Your heart just breaks, that’s all,” her June 2015 caption read. “Heartbreak is hard but you find more and more things to be grateful for every day,” she continued.

“One of those things is all of you,” she added. “Thank you all. Yes I’m going to be okay and I love u guys so so much. Everyday is a blessing.”

Danny Amendola

Olivia and the NFL wide receiver had quite the toxic relationship from April 2016 to March 2018. After their breakup, Danny posted a lengthy rant on Instagram, deep diving into their past relationship.

“I believe there should be a boundary btw private life and social media. Olivia believes in fishbowl lifestyle. This fundamental difference was huge in our relationship,” he said.

“Olivia chooses and wants to be noticed on the internet and in Hollywood to make money. Which was hard for me to understand but quickly had to learn. Whereas the cost of fame in this world doesn’t appeal to me. I play ball for one reason and that’s RESPECT.”

Christian McCaffery

Olivia and the NFL star first sparked dating rumors in May 2019, while they announced their engagement nearly four years later in April 2023.

“We tried to keep this quiet for as long as possible but apparently word travels fast,” she wrote via Instagram at the time. “I’m marrying my best friend, I love you so much, fiancé.”