Harry Styles and Emily Ratajkowski are both big names in the entertainment industry, but for very different reasons. Styles is a very popular singer who got his start in the boy band One Direction. Now, the singer is a very successful solo artist who not only sells out tours, but also has won Grammy Awards for his work. Ratajkowski, on the other hand, is a model who dabbles in acting. She recently divorced Sebastian Bear-McClard after discovering he was cheating on her, and now she is seeing Styles.
Styles and Ratajkowski have been seen kissing and hanging out, and fans are very interested in the pairing. Styles has also been in several high-profile relationships over the years, most recently with Olivia Wilde. His former relationship with Wilde may be causing turmoil in his new relationship with Ratajkowski. Let’s get into the relationship timeline of Harry Styles and Emily Ratajkowski.
8 Who Is Harry Styles?
Harry Styles is a singing sensation. He first rose to popularity in 2010 when he competed on The X Factor as a member of the band One Direction. The group became extremely popular worldwide, though they disbanded in 2015 shortly after Zayn Malik announced that he would be leaving the boy band. Now, the members of the former band are attempting solo careers, and Styles is overwhelming the most successful.
Styles has sold out tours and recently won the Grammy Award for Album of the Year and Pop Vocal Album of the Year for his 2022 album Harry’s House. The wins were unfortunately surrounded by backlash, as some fans thought that Beyoncé deserved to win Album of the Year and his acceptance speech was taken by many as an example of white privilege.
7 What Taylor Swift Songs Are About Harry Styles?
As a high-profile celebrity, it is no surprise that Harry Styles as a long list of famous exes. Over the years, Styles has dated several models, including reality star Kendall Jenner. He reportedly dated Jenner during two separate occasions. One of his more famous exes, and one that is continued to be discussed to this day, is Taylor Swift.
Styles and Swift dated briefly from 2012 to very early 2013. Though a brief love affair, that did not stop Swift from writing several songs about the former One Direction member. Fans speculate that songs such as “Style,” “Out of the Woods,” and “I Knew You Were Trouble” are about Styles. Recently Swift released the album Midnights, which includes songs written over the past decade. Fans thing the song “Maroon” from the new album is also about Styles.
6 Harry Styles Dated Olivia Wilde

Harry Styles’s most recent famous relationship was with actress and director Olivia Wilde. The two met while creating the movie Don’t Worry Darling, which was not well-received by critics. A lot of drama surrounded the production and release of the film, and the fact that Styles and Wilde were dating behind the scenes certainly did not help the film’s popularity.
Styles and Wilde dated from 2021 to late 2022. They were first seen at a wedding holding hands, which shocked many fans. The pairing seemed off from the beginning, so when news broke that they had split in November 2022, fans were not surprised. Though no longer together, Styles’s former relationship with Wilde may be causing friction in his new relationship with Ratajkowski.
5 Who Is Emily Ratajkowski?

Emily Ratajkowski is an actress and model. She got her start in the entertainment industry as a young child, appearing in two episodes of the children’s show iCarly. She made her modeling debut in 2012 on the cover of an erotic magazine. Ratajkowski then went on to appear in music video’s such as Robin Thicke’s “Blurred Lines” and Maroon 5’s “Love Somebody.” Since then, her career has taken off in modeling and acting.
Ratajkowski tied the knot with Sebastian Bear-McClard in 2018. She had only been dating him for a few weeks when they had their courthouse wedding. Ratajkowski gave birth to their son in March 2021, but a year later she separated from her husband. The model and actress has since come forward to reveal Bear-McClard’s infidelity as the cause for their divorce.
4 Emily Ratajkowski Divorced Cheater Sebastian Bear-McClard

As previously mentioned, Emily and Ratajkowski married actor Sebastian Bear-McClard in 2018 after just a few weeks of dating. All seemed to be going well for the couple, and they welcomed a baby boy in March 2021. Sadly, their relationship and marriage was not meant to be. Ratajkowski discovered that Bear-McClard was cheating on her with multiple women over a long period of time, and she made the tough decision to split up their family.
“Yeah, he’s cheated,” a source revealed to Page Six at the time of their divorce. Ratajkowski separated from Bear-McClard in July 2022 and filed for divorce that September. “He’s a serial cheater,” the source continued, implying that there were multiple women and that the cheating was ongoing. “It’s gross. He’s a dog.” Ratajkowski is now adjusting to single life and focused on raising her son.
3 Harry Styles Is “Thrilled” To Hook Up With Emily Ratajkowski

After the heartbreaking split from Sebastian Bear-McClard, Emily Ratajkowski is back in the celebrity dating pool. Following her divorce, Ratajkowski has been seen out with several men. She was briefly seen with Brad Pitt, Pete Davidson, and DJ Orazio Rispo. The model and actress is trying to have fun, and now she is having fun with one of the most popular male singers of this generation.
“Harry has always been very attracted to Emily,” a source revealed to Us Weekly. The new couple began being seen together in March 2023, and they seem completely enamored with each other. The source also revealed that Styles is “thrilled” about “hooking up” with the model. They do not seem to be putting a label on the nature of their relationship, so time will tell what comes of the new couple.
2 Harry Styles And Emily Ratajkowski Are Having Fun
It is no surprise that recently-divorced Emily Ratajkowski is not looking for a serious relationship. She was married to Sebastian Bear-McClard for roughly four years, and the nature of their split was surely incredibly traumatic. The model and actress is on the market for casual dating, hence why she has been spotted going out with so many different celebrities. Ratajkowski wants to enjoy light dating for a while before diving into anything remotely serious.
Her relationship with Harry Styles may be exactly what she’s been looking for. The two are certainly having a lot of fun together, and they’ve even traveled the world a bit. Ratajkowski joined Styles in Tokyo. They were spotted kissing in Japan, and a video of the PDA went viral. Ratajkowski and Styles are very comfortable around each other as they have known each other for a while.
1 Olivia Wilde Feels Betrayed By Emily Ratajkowski
Harry Styles’s former relationship may be coming back to bite him. He dated Olivia Wilde for well over a year, only just breaking up with the actress and director in November 2022. Though it was an amicable split and they claim to still be friends, Wilde is certainly not happy about who Styles is choosing to spend his time with post-breakup.
Wilde and Emily Ratajkowski are known to be friendly with each other. They have been seen hanging out many times. They were actually seen hanging out at one of Styles’s concerts in June in Paris. Wilde and Styles were still together at the time. Ratajkowski and Wilde were most recently seen together at the Vanity Fair Oscar Afterparty on March 12th, 2023. A source close to the two friends told Page Six that Ratajkowski’s new relationship with Styles “is a betrayal” and that Ratajkowski is “begging for forgiveness” from Wilde.
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