When it comes to love in the limelight, Reese WItherspoon is a veteran. From flying across the country to see her one-time beau Chris O’Donnell, to forming a blended family with her two ex-husbands, she’s had a long storied history of romance in the public eye. But it hasn’t all been windswept love stories for the “Legally Blonde” actor.
She has endured two divorces, a series of dating rumors, and has even had to escape from an abusive relationship in her past. Despite it all, she has found her voice and is able to speak up for what she wants and deserves both in a relationship and life. “Leaving those situations [isn’t] easy because it’s wrought with self-doubt, particularly if someone damages your self-esteem,” she once said of her past abusive relationship in an episode of “Oprah’s Super Soul Conversations.” “…I didn’t have self-esteem, you know? And I’m a different person now.”
She and Jeremy Sisto had a long-distance relationship as young actors
While she was starting to make her way through Hollywood, Reese Witherspoon was amongst a chock-full dating pool of fellow up-and-coming actors. The actor that Reese Witherspoon dated before future husband Ryan Phillippe was Jeremy Sisto, best known in the ’90s as the greasy Elton in “Clueless.” The two met on the set of the 1992 TV film “Desperate Choices: To Save My Child,” where the two played boyfriend and girlfriend on screen. “She was my first actress girlfriend,” Sisto admitted in a Reddit AMA (via Yahoo!). “…I was so into her.”
Witherspoon hasn’t spoken much about their young love affair publicly, but Sisto shared details about their relationship – including the miscommunication that led to their permanent breakup. While Witherspoon went to Africa to film a movie, Sisto had assumed that the pair had broken up and went on to date his eventual wife. But when the “Sweet Home Alabama” star returned to the United States, she didn’t realize that the pair had called it quits.
But the stars seemed to brush away any bad feelings. They even almost starred together in “Clueless,” as Witherspoon was up for the lead role of Cher Horowitz. While that didn’t pan out, Sisto has nothing but love for his former flame. “She’s a great person,” he gushed on the Reddit AMA.
She fell in love with Ryan Phillippe on set and off
Many think that Reese Witherspoon and Ryan Phillippe first met on the set of 1999’s “Cruel Intentions,” but it was actually the “Walk The Line” star’s 21st birthday that initially sparked a romance for the pair. As Witherspoon recalls it, she locked eyes with her future husband after some celebratory cocktails. “I don’t know what came over me — maybe the seven Midori sours — but I told [Ryan], ‘I think you’re my birthday present,'” she admitted to Jane Magazine (via US Weekly).
The on-screen love interests took their romance off-screen following the release of “Cruel Intentions,” and got married in a South Carolina ceremony in June 1999. Despite the fast relationship timeline, Witherspoon was confident in their partnership. “I’ve always believed that you should know who your life partner should be from the first moment you meet,” she shared with Cinema.com. “That’s how Ryan and I felt about each other from the beginning and so we’ve always been very secure in our feelings.”
She raised a family with Ryan Phillippe before things went south
During her marriage to Phillippe, Witherspoon starred in the career trajectory-changing film “Legally Blonde,” which catapulted her to “America’s Sweetheart” status in 2001. But that wasn’t all that happened around the turn of the century – the starlet also gave birth to the pair’s two children, Ava and Deacon. The actor had to rely on Phillippe more than ever on the set of “Legally Blonde” as she balanced her day job and new motherhood. “…There were a lot of days when I didn’t think I could pull it off,” she shared with Cinema.com. But her husband was there to take care of their daughter and assuage his wife’s fears as she worked day and night in her dual roles. “That’s exactly the kind of reassurance I needed.”
But the balancing act between the pair didn’t last, as the pair got divorced in 2006. Based on Witherspoon’s reaction to his awkward Oscars comment in 2002, in which he shared with the crowd that Witherspoon made more than him, tension had been growing for a while. It was also rumored that Phillippe cheated on Witherspoon with future girlfriend Abbie Cornish.
Witherspoon has gotten candid about her divorce from Ryan Phillippe, saying that she spent months trying to find her footing in both her career and in life. “You can’t really be very creative when you feel like your brain is scrambled eggs,” she explained in a “60 Minutes” interview in 2014 (via People). Now, the two have co-parented their children and found peace with each other. “I knew that even if we didn’t make it, she would be a great person to raise kids with,” he once told The Guardian. “…I respect and admire her, and we made some pretty great and beautiful kids.”
She found post-divorce love with co-star Jake Gyllenhaal
During her divorce, Reese Witherspoon found companionship with her “Rendition” co-star Jake Gyllenhaal. Inside Witherspoon and Gyllenhaal’s relationship, the pair hit it off on set but took some time apart as the “A Wrinkle In Time” actor finalized her split from Ryan Phillippe. Afterward, she reunited with Gyllenhaal and things got serious for a few years. She admitted she learned from her previous relationship and came into her own as she navigated this relationship. “As you get older, you know what you like and what you don’t like, and you’re not apologetic about it,” she told InStyle (via NBC5 Dallas-Fort Worth). “I definitely feel much more confident in it.”
The pair’s time together, which became rooted in home cooking and living life in the moment, ended in 2009. Gyllenhaal allegedly was anxious to get married, but Witherspoon (and her kids) were reportedly not ready for that step, leaving the actor heartbroken. “…I don’t know how I feel about marriage,” she told Parade at the time (via People). “Obviously, I’m not far enough out of being married to think about doing it again.”
She became a married woman again with Jim Toth
Reese Witherspoon changed her tune about marriage when she wed talent agent Jim Toth in 2010. After meeting Toth “out of the blue” at a party shortly after her split from Gyllenhaal, the duo’s courtship progressed quickly, and they were engaged by the end of that year. But despite the quick progression, things felt different with Toth at her side. “Jim said, ‘I’m gonna show you every day what a good partner is, what a good person is. I’m going to take care of you. I’m gonna do this so much that you’re gonna get used to it,'” she gushed to Elle in 2012. “…I’ve never had anybody like that in my life.” The pair were married in an intimate backyard wedding in 2011, where the “Wild” actor’s daughter Ava served as the maid of honor.
Despite the naysayers who cautioned Witherspoon about finding a partner who accepts her children from other relationships, the star affirmed that she was confident in who she chose to love. “I was determined to find somebody who would make that not true,” she said in an interview with Marie Claire in 2010. “And I got lucky.”
History repeated itself with a new baby and new divorce from Jim Toth
Reese Witherspoon and Jim Toth’s love brought about a new life when their son Tennessee was born in September 2012. Even though she was already a mother, her third child brought about a new confidence in Witherspoon regarding her mothering skills. “I feel more confident—I’ve been doing it for 23 years— [and] I probably got some stuff right,” she admitted to E! News.
That wasn’t the only similar life event that happened in this relationship of Witherspoon’s. While there were some strange things about Witherspoon and Toth’s marriage, the pair stayed together for almost 12 years before the “Sing” star filed for divorce in 2023. “We have enjoyed so many wonderful years together and are moving forward with deep love, kindness and mutual respect for everything we have created together,” they shared in a joint statement in a since-deleted Instagram post (via Cosmopolitan).
Unlike her last divorce, Witherspoon was determined to control her narrative rather than let the press speak for her. “…It feels much more authentic to be able to say things in my own voice and not let somebody else control what’s happening,” she told Harper’s Bazaar.
She found new love with Oliver Haarmann
Reese Witherspoon moved on quickly after her divorce from Jim Toth, and she has never been one to leave love on the table for long. In 2024, she was rumored to have started dating financier Oliver Haarmann. Unlike her other relationships, the pair allegedly took things slow from the start as she maintained her family focus. “She enjoys [the relationship] but doesn’t want it to be a big focus,” a source told People. “She’s busy with work and her son,” says the insider. “These are her biggest priorities.”
The actor hasn’t publicly commented on her relationship with Haarmann, but sources shared she’s enjoying a quiet life with her new beau. She’s even been flying from her new hometown of Nashville, Tennessee to see him in New York City, all while balancing her priorities as a performer, producer, and parent. The two have been spotted on dinner dates around the city, but haven’t been photographed publicly at any A-list events. “Reese loves that he’s a businessman and not into Hollywood,” a source shared with People.
She’s had her fair share of rumored flings
As any A-lister is prone to have, Reese Witherspoon has fared a few rumors of flings with fellow famous folk. She’s been linked to fellow actor Kevin Costner, with whom she was reportedly casually dating in late 2024. But the “A Wrinkle In Time” actor’s reps quickly shut down the rumors. “This story is completely fabricated and not true,” her team told Page Six. Neither she nor Costner have publicly commented about their alleged affair.
She’s also been rumored to have dated NFL Hall of Famer Tom Brady, which both famous folks’ reps have shut down. Both stars were fresh from divorcing their longtime loves (Toth and Brady’s ex-wife Gisele Bündchen) and haven’t spoken publicly about the rumors. In the face of all of the rumors thrown her way, Witherspoon maintains one particular piece of advice that she holds close: “Run away from a man who can’t handle your ambition,” she once shared in an essay for Glamour.
