The former Miss Universe dated the Jonas Brothers singer for nearly two years, during which Jonas penned his hit song inspired by Culpo. After her split with Jonas, Culpo was linked to a few different high-profile athletes before she ultimately found love with San Francisco 49ers running back Christian McCaffrey, whom she's been in a relationship with since 2019.
While she's found happiness, Culpo hints in her TLC reality show The Culpo Sisters that her love life hasn't always been so rosy.
"I worry all the time about the future. I always thought by 30 I would be married [and] I'd have kids," she said. "I was with somebody that did really horrible, horrible things. I was made to feel like a less-than human in every sense of the word. I've never talked about it before."
However, as she told PEOPLE StyleWatch for her November 2022 cover, her past has helped her appreciate her current relationship with McCaffrey.
"I think every single relationship teaches you so much about yourself, and I definitely have an appreciation for my relationship now that I would never have because of all of my past experiences, so you have to be grateful for the rough s—," she said.
From her rumored flings to her long-term relationships, here's a look back at Olivia Culpo's dating history.
Were they, or weren't they?
In September 2012, Olympian Ryan Lochte was reportedly smitten with Culpo. He told E! News at the time, "She is beautiful. I love hanging out with her. She has a great sense of humor. She makes me laugh. She's just a good girl to hang out with."
However, Culpo didn't seem quite as enamored with the swimmer, telling the New York Post that she and Lochte were just friends and that she was single. "People make things up when they see people together," she said.
Culpo and Jonas first started dating in 2013, and the Rhode Island native moved to Los Angeles to be with the "Sucker" singer.
In April 2015, Jonas praised Culpo for improving his life overall, telling PEOPLE, "I think anytime you have a teammate it makes things a little easier. It has been a wild ride and a crazy year and a half. It's been really special." He also noted that strangers ogling her inspired his hit song "Jealous."
That June, Jonas told PEOPLE he's "no pro" at long-distance relationships while he's touring, explaining, "It's just about trying to take it one step at a time. I think that the long-distance thing can be tough, but try to stay in communication, keep it transparent and honest, and it should be okay."
Just one week later, news broke that the pair had split, with a friend of Jonas saying the breakup had been "tough" for the model and the singer.
For her part, Culpo remained mostly mum about her relationship with the singer until she opened up about the split and its aftermath on her reality series The Culpo Sisters in November 2022.
"I did date Nick and that was a very formative experience for me," she said. "I moved to L.A. with him. I had no brand, no money and I was in love. That was great, right? But when he broke up with me, I was kind of left with no sense of identity. My whole identity was in him, which is a very common story of a young person in love."
Culpo added that she believed she and Jonas would get married someday, and that she struggled to afford her lifestyle after their breakup.
"I just remember night after night looking up at my ceiling in my apartment that I couldn't afford thinking to myself how am I going to pay my rent," she said. "I couldn't even afford my groceries."
Still, she's thankful for the experience, explaining, "It was a serious, pivotal moment for me, but it was something that taught me that you can't give up." She also previously told PEOPLE that she was thrilled about Jonas and his now-wife Priyanka Chopra's engagement. "I think that any time anybody can find love, especially in this industry — because it's difficult, you can see there's a track record of things not working out. So I'm so happy for him."
After her split from Jonas, Culpo was briefly linked to NFL quarterback Tim Tebow. According to E! News, the pair began dating sometime in September 2015 and did their best to keep their romance under the radar while they got to know one another.
Whatever connection they had reportedly fizzled by that November, however, with sources telling TMZ that the pair never actually dated. According to the outlet, they hung out together with groups of mutual friends after meeting at church, but never had any solo outings.
Incidentally, Tebow went on to marry a different brunette Miss Universe, Demi-Leigh Nel-Peters, in January 2020.
Culpo and then-New England Patriots wide receiver Danny Amendola first became Instagram official in February 2016. By March 2018, Culpo confirmed that the couple had split, but they appeared to have reconciled at a mutual friend's wedding that June.
In October 2018, Amendola was spotted getting close with CBS Sports reporter Bianca Peters while he and Culpo were reportedly still together. A source told PEOPLE at the time, "Danny and Olivia did not officially split. Danny is playing both sides. He's saying that the day with Bianca was just him having fun. She's a reporter, he's a football player. I think in his mind he got caught so he's trying to diffuse it."
The insider noted that Culpo and Amendola were apparently on two different pages when it came to their relationship, saying, "Danny never viewed Olivia as an exclusive girlfriend."
In early November 2018, Culpo posted an Instagram Story wearing a Rolex it's speculated she bought for Amendola's birthday, with the caption, "Looks like this is my present now. HAPPY BDAY TO ME." Despite the post, Culpo and Amendola appeared to reconcile by New Year's Eve, though neither confirmed a rekindling, and their relationship ended for good by April 2019.
Culpo was first linked to Zedd in April 2019 after TMZ shared a video of the DJ and model dancing with their arms around one another to Ariana Grande's "God Is a Woman" at Coachella. He was also on hand to celebrate her birthday in May 2019, with reports saying he was by her side throughout a dinner party in her honor.
Though the fling was seemingly short-lived, it was highly publicized due to Amendola's reaction. After Culpo and Zedd got cozy at Coachella, Amendola posted an Instagram Story that shaded the "True Colors" hitmaker. He later posted a long Instagram rant, calling Culpo "f—ked up" and saying that her desire for publicity doomed their relationship; he also referred to Zedd as a "scrony [sic] little f—er." Amendola later deleted the diatribe and wrote, "People won't often remember what you said, they will remember how you made them feel."
Culpo is currently dating NFL player Christian McCaffrey, and she broke one of her own cardinal dating rules for him: "no athletes ever again."
"He's just the best, I feel like he is really everything that I could ever ask for, so I never have to worry about anything," she told Entertainment Tonight in November 2022. "I think that was the reason why I didn't want to date an athlete, no offense, because there is a reputation there."
Culpo was first linked to McCaffrey in 2019 after he liked one of her Instagram posts. By July 2019, they enjoyed a Cabo getaway together with friends.
In October 2019, Culpo was photographed wearing one of McCaffrey's jerseys to a game, and on Nov. 3, 2019, he posted an Instagram Story about how proud he was of Culpo for her Sports Illustrated Swimsuit shoot. Later that month, McCaffrey posted another story of Culpo and his mom cheering him on at a game. Several more sightings followed, and on Feb. 1, 2020, they made their red carpet debut as a couple at the NFL Honors.
They were fully Instagram official by Valentine's Day 2020, when Culpo posted a sweet tribute to McCaffrey, calling him her "best friend." They've since gotten a puppy together and celebrated their three-year anniversary on June 22, 2022.
Culpo discussed her future with McCaffrey during an episode of The Culpo Sisters, explaining that she and the running back aren't quite ready to have kids yet.
"I've talked to Christian and we're on the same page about having kids, we both want to have kids, but the timeline of that is something that is not in the foreseeable future," she said. "He is completely and totally focused on football and he should be. He's not ready to have kids. It's not really an option."
Culpo also opened up about how she feels she has a "ticking time bomb" when it comes to her fertility given her endometriosis diagnosis and the couple's four-year age difference.
"I'm so worried about putting pressure on my relationship in a way that's not going to move it in the direction that I want," she shared. "But that's also not who I am. I don't want to feel like I have to do certain things to reframe my life in a way that's going to move it toward a ring on my hand. I just can't imagine having to start over again."
While speaking with StyleWatch, Culpo reiterated that though she wants to start a family with McCaffrey, watching her sister Aurora Culpo parent her two kids is a "really good form of birth control."