All About Emily Ratajkowski's Dating History, From Sebastian Bear-McClard to Harry Styles

In July 2022, Emily Ratajkowski split with her former husband Sebastian Bear-McClard. The pair were married in 2018 and share one child, a son name Sylvester Apollo, who was born on March 8, 2021. Following her divorce, Ratajkowski told Harper’s Bazaar that she was enjoying being single and embracing the dating scene.

“I can tell you that I have never been single before,” the model explained. “I feel all the emotions. I feel anger, sadness. I feel excitement. I feel joy. I feel levity. Every day is different. The only good thing I know is that I’m feeling all those things, which is nice because it makes me believe that I’ll be OK.”

Ratajkowski admitted she used to be a “pick-me girl” because she “wasn’t very good at deciding what I liked.”

“I really wanted to be chosen,” she went on. “It was hard for me to go on a date with someone and think about how much I did or didn’t like them. I would have been thinking about how they were perceiving me, what it meant, what they wanted from me, what it meant about my self-worth.”

She added, “I don’t have that anymore. So now it’s really fun to go to dinner with someone and be like, ‘Cool. I really enjoyed these parts of them. I really didn’t like these other parts.’”

Since her divorce, the model has been linked with a number of people and seems to be enjoying herself and figuring out what she likes. Here’s her complete dating history so far, from before Bear-McClard to after.

Andrew Dryden: 2013-2014

After her appearance in Robin Thicke’s “Blurred Lines” in 2013, Ratajkowski started to be a much more recognizable figure in the entertainment industry. Her first public relationship then was with Andrew Dryden, a creative director and menswear buyer in Los Angeles at the time. But they weren’t in public much, and things ended in less than a year. The Inamorata designer dodged question about their breakup in February 2014, while she was supposedly at a Super Bowl party telling people she was single.

All Dryden would say was, “Sorry, I don’t want to talk about it.”

Jeff Magid: 2014-2018

Magid is a Los Angeles musician who was first seen with Ratajkowski in December 2014. They dated for three years, allegedly even living together before breaking up in January 2018. New York Daily News spoke with a source who said they hadn’t been sharing a home in “weeks.”

“They were living together at his downtown L.A. apartment in the trendy Arts District,” the insider added. “While Emily did not make a big deal publicly about them living together, it was common knowledge among her friends.”

The source continued, “They used to be inseparable, although she tried to play down things in public.”

Sebastian Bear-McClard: 2018-2022

The reason behind Ratajkowski and Magid’s split may never be known, but it is often inferred that it had something to do with Sebastian Bear-McClard. In February 2018, one month after her breakup with Magid, Ratajkowski announced she was married.

She shared the news in her Instagram Stories, writing, “Sooo, I have a surprise, I got married today.”

A source said that she and Bear-McClard “were all in a friend group” and that he “wasn’t a stranger” to explain the whirlwind romance. Their son was born in March 2021.

The couple reportedly split in July 2022, and Ratajkowski filed for divorce in September 2022. It was rumored Bear-McClard had cheated on her. She got a new place, and they reportedly only spoke through their nanny.

“She isn’t speaking to him because of his [alleged] infidelity, he isn’t speaking to her because he feels she was checked out of their relationship for the last year,” a source told Us Weekly. “She got an apartment downtown to get away from her ex and start her new life. They’re only speaking to each other through the nanny.”

Brad Pitt: September-October 2022

In September 2022, the model was linked to actor Brad Pitt.

“[They are] getting to know each other,” a source said at the time. “Brad and Emily have been hanging out as friends. But they like each other and are excited to see where things go.”

They went on a few casual dates, a source told People.

“[Pitt] was introduced to Emily by a friend in the art world. There is an attraction, but nothing serious going on,” the source said. “She is obviously gorgeous and very into art as well. They have a lot to talk about and always have a great time when they hang out. They stay in touch when they don’t see each other.”

Things seemed to have fizzled out by October, and in November, Pitt was dating his current girlfriend Ines de Ramon.

Orazio Rispo: October 2022

Amongst the Pitt rumors, Ratajkowski was photographed in New York City kissing DJ Orazio Rispo, so they went out at least once. They were seen together again in June 2023 but not kissing this time.

Pete Davidson: November 2022

In November 2022, a source told Us Weekly that Ratajkowski and comedian Pete Davidson were dating after they were introduced by a mutual friend.

“Pete makes Emily laugh, and he loves how intelligent she is,” they said, before claiming the pair had been seeing each other for “a couple of months.”

But in December, things had cooled down, and another source told People it was always just for fun.

“Em is single and totally happy,” they said. “She will always prioritize her son, but enjoys dating when she has time. She enjoys her independence. She doesn’t have plans to see Pete again. She had fun with him, but she realized she didn’t want it to become anything else. She likes her life as it is.”

Jack Greer: December 2022

That same month, she was photographed kissing artist Jack Greer outside her apartment.

Eric Andre: January-February 2023

Continuing with comedians, Ratajkowski was seen with Eric Andre in early January 2023 walking around Midtown Manhattan. At the end of the month, they were sharing some kisses in the Cayman Islands. An eyewitness said, “Emily and Eric were looking pretty cozy on the beach, lounging by the waterfront. They were kissing and flirting. He was cracking jokes and making everybody laugh.”

They added, “It seemed like a fun friends-with-benefits situation. They hung out at the bar, drinking cocktails and chatting with everyone. They just seemed really happy and relaxed together.”

Around Valentine’s Day, Andre shared a photo of himself in the nude with Ratajkowski, also in the buff. The post has since been deleted.

In March, a source told E! News that Ratajkowski “broke up with Eric days before he posted that photo,” adding, “She had nothing to do with the posting.”

Andre said in an interview with Rolling Stone that month that they took the picture when in “the moment.”

“I was drinking wine, she started dying laughing, and she was like, ‘I have to take a picture of this,’” he recalled. “She took the picture, we both started cracking up, and she was like, ‘This is iconic’—she kept saying ‘iconic.’ We both agreed this was a beautiful image that we had to share with the world.”

He added that the attention they garnered was difficult.

“It’s more about how I feel concerned for her safety and the safety of others at her level who deal with that...She’s handled it with grace,” he said.

Harry Styles: March 2023

In March 2023, Ratajkowski was seen kissing singer Harry Styles in Tokyo, shortly after he split from longtime girlfriend Olivia Wilde. In an interview with Spanish Vogue in April, the model discussed the viral moment and fan response on social media.

“It’s very bizarre to have certain experiences and then have the whole world know about them and comment on them,” she said. “I’m just a person who’s gone from a three-year relationship to a four-year relationship.”

She went on, “So this is the first time in a long time that I’ve been in a dating stage...The interest there is in that particular area is very strange. Not that I’m surprised, but it’s a tiny slice of my life. Most of my life is focused on my son and my work.”

Of the images of her with Styles specifically, she said, “I didn’t expect this to happen. I think, in general, there’s a reason certain celebrities live in [Los Angeles], hire security, don’t go to public restaurants…So the idea of giving [my freedom] up for the sake of privacy is something I haven’t considered yet.”

When asked of the rumors that she and Wilde had a feud over Styles, Ratajkowski suggested it was just fictional female rivalry and then seemed to allude to Wilde’s alleged conflict with actress Florence Pugh.

“It’s more of the same,” she said. “I feel bad for Olivia [Wilde] because she has had to suffer this situation on several occasions.”

Shaboozey

In the summer of 2024, Ratajkowski was rumored to be dating country music star Shaboozey, whose given name is Collins Chibueze. It is possible they met at Michael Rubin’s annual Fourth of July White Party in the Hamptons, according to the Cut. They were seen grabbing dinner together at Maison Close in SoHo a few weeks later and then at Rema’s album-release party, holding hands. Page Six reported that the pair were seen enjoying some PDA at New York City nightclub Musica int August. Later, the model was seen during Shaboozey’s performance at the Z100 Summer Bash and attending a screening of Blink Twice together. There have not been any other sightings almost nine months later, but since the pair never confirmed they were dating, there’s also no info about a breakup.