Reese Witherspoon Makes First Public Appearance With Boyfriend Oliver Haarmann at 'Elle' Premiere
Hard-launching a romance at the same time as a highly anticipated new series? What? Like it's hard?
Good thing Reese Witherspoon—much like tighty-whities contest judge Elle Woods—can handle anything. Nearly two years after the actress, an executive producer on Prime Video's Legally Blonde spinoff Elle, was first seen with German financier Oliver Haarmann out in New York City, she invited the billionaire businessman to be her plus-one at the prequel's June 23 premiere.
And, yes, for those wondering, he did get into Harvard, where he earned an MBA after graduating from Brown University.
Starting at global investment firm KKR, Haarmann co-founded private equity firm Searchlight Capital Partners in 2010. He also owns a minority stake in NHL team the New York Islanders and a piece of Witherspoon's heart.
A year after the Oscar winner, 50, and the 58-year-old first stepped out—flying into NYC on a private helicopter—they enjoyed a romantic yacht outing off the coast of Saint-Tropez in July 2025.
Most importantly, the dad of two understands that whoever said orange is the new pink was seriously disturbed. Because he selected an on-theme pink tie for his appearance at the Elle premiere in New York. (The Prime Video series drops July 1.)
After all, it's important that Witherspoon, much like her beloved character, not have a boyfriend that's such a complete bonehead.
Not that her past romances are particularly worthy of objection.
Take ex-husband Jim Toth, the CAA agent who would give "me pep talks with a lot of sports metaphors that I don’t always understand," Witherspoon detailed in a 2017 Glamour essay, stressing that women shouldn't settle for anything less. "Run away from a man who can’t handle your ambition," she urged. "Run. So many men think ambition is awesome and sexy!"
The evidence is in the Hello Sunshine co-founder's dating history that includes first husband Ryan Phillippe (dad to Ava, 26, and Deacon, 22), Toth (they share son Tennessee, 13) and Oscar nominee Jake Gyllenhaal.
Allow us to present our case.
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Chris O'Donnell: Just Rumors
The two were romantically linked in 1993 after a then-16-year-old Reese Witherspoon accompanied Chris O'Donnell, 22 at the time, to a tribute party for his Scent of a Woman co-star Al Pacino in New York City. But neither Witherspoon nor O'Donnell ever confirmed a relationship.
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Stephen Dorff: Just Rumors
When Witherspoon and Stephen Dorff starred in the 1994 movie S.F.W. (which stands for "So F--king What") it kicked off dating rumors. Witherspoon's response? No f--king way.
"I wouldn't date Dorff for all the money in the world," Reese told Details magazine in 1995. "I really admire the girls who do hold Dorff's attention. I don't know if it's because he doesn't know what he wants, or that he knows exactly what he wants and if that person doesn't apply, he's going to find it somewhere else. You have to be comfortable giving him space. I'm not that kind of girl."
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Thanks to their red hot chemistry in the 1995 thriller Fear, fans were eager to see Witherspoon and Mark Wahlberg pair off IRL. But we're afraid neither ever confirmed a relationship.
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Ryan Phillippe: Divorced
Despite popular belief, Witherspoon did not meet future husband Ryan Phillippe on the set of the 1999 film Cruel Intentions. Rather, "I crashed her party," Phillippe explained to Pennsylvania newspaper The Morning Call of attending her 21st birthday bash, weeks before getting the script. "I went with a friend because I knew there would be free food and drinks. I was just sitting back in the corner pounding away the drinks when somebody walked over and introduced Reese to me."
That's when she made her move.
"I don't know what came over me—maybe the seven Midori sours—but I told him, 'I think you're my birthday present,'" she recounted to Jane magazine in 1998. "He thought it was so flattering, and now that I think about it...how embarrassing!"
Later, when Cruel Intentions director Roger Kumble "was hanging out with Ryan one night," he recalled to Cosmopolitan, they began discussing who should be cast as his girlfriend, "and I was like, 'What about your girlfriend?'"
After some convincing ("She wanted to strengthen the character, and she was right," noted Kumble), Witherspoon signed on. The couple wed three months after the film's release, going on to welcome daughter Ava Phillippe in 1999 and son Deacon Phillippe in 2003 before separating in 2006. 'Cause it's a bittersweet symphony, that's life.
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After co-starring in the 2007 thriller Rendition, Witherspoon and Jake Gyllenhaal dated for two years before announcing their split in 2009.
"He's very supportive," Witherspoon told Vogue in 2008. "Suffice it to say, I'm very happy in life, and I'm very lucky to have a lot of really supportive people around me who care very much for me, and, you know, that's all you can hope for in life. I am very blessed in that way."
Jim Toth: Divorced
Witherspoon wed CAA talent agent Jim Toth in 2011 after dating for a year. But more than a decade after welcoming son Tennessee Toth in 2012, they stunned fans by announcing their split. "We have enjoyed so many wonderful years together," they shared in a joint March 2023 announcement, "and are moving forward with deep love, kindness and mutual respect for everything we have created together."
Going through her second public divorce, "To be able to talk to people directly about what’s going on in my life and just share it in the way that I share great professional experiences or personal experiences, it feels much more authentic to be able to say things in my own voice," Witherspoon detailed to Harper's Bazaar months later. "Then, of course, there's speculation, but I can’t control that. All I can do is be my most honest, forthright self and be vulnerable."
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Oliver Haarmann: Dating
No objections were lodged when Witherspoon officially debuted her romance with German financier Oliver Haarmann at the June 2026 premiere of her Legally Blonde spinoff Elle.
Though by then she and the founding partner of Searchlight Capital Partners, a dad of two, had already presented plenty of evidence about their romance. First spotted out in New York City in September 2024, they also enjoyed a getaway to Saint Tropez in July 2025.
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