Reese Witherspoon has been making headlines this week. First, she shocked Jennifer Aniston by revealing her real name on camera, and now she’s got everyone talking about her past relationships. During a recent interview with the New York Times’ podcast, The Interview, Witherspoon said that she had to “rewire” her brain after leaving an abusive relationship. It is one of the first times she’s mentioned being involved in an abusive pairing, though she’s been divorced twice while a public figure.  Witherspoon hinted that she was “very young” when the relationship happened, but she didn’t name any names. Now, everyone is clamoring to remember all of the men she dated. We have a list.

Reese Witherspoon got into her first relationship after her first major acting job

Reese Witherspoon has been acting since she was a child, but her big break came in 1991 when she was just 14 years old. The role in The Man in the Moon predated her first relationship. Apparently, a few years after starring in the film, Witherspoon met fellow actor Jeremy Sisto. The pair had a teenage romance that lasted for a “long time,” Sisto told fans on Reddit during an AMA event.

Sisto, who is currently starring in FBI, may also be remembered as Elton in Clueless. He said he met Witherspoon on set and that they carried on a long-distance romance before she eventually went to film in Africa. He claims he thought they had broken up, but later found out Witherspoon hadn’t intended it. The actor appears to believe he fumbled, insisting he feels bad about the situation and still holds Witherspoon in high regard. Witherspoon would have been about 16 while Sisto was around 17 at the time.  

After Sisto, Withet hrspoon was rumored to have had a brief relationship with Stephen Dorff. Witherspoon shot down that rumor herself in 1995, claiming that she wouldn’t date him for “all the money in the world,” because he needed a girl who could “give him space,” and that was not her style.

She married Ryan Phillip as a young adult

While Witherspoon’s dating career began at a pretty average age, she married exceptionally young, considering her high-profile career. Witherspoon and fellow actor Ryan Phillippe met at her 21st Birthday party and fell in love quickly. They met in 1997 and were married by the end of 1999. They welcomed their daughter the same year and a few years later announced the birth of their son. Witherspoon and Phillippe announced their plans to divorce in 2006. Though it’s unclear what went wrong between the pair, infidelity rumors ran rampant at the time.

Witherspoon and Phillippe seem to have a civil relationship now, but he’s run into trouble in other relationships. In 2017, his ex-girlfriend, Elsie Hewitt, sued Phillippe. In the filing, she claims he violently attacked her during a fight. They settled privately. Hewitt is currently dating Pete Davidson and is expecting their first child together. She previously dated Benny Blanco.

Reese Witherspoon and Jake Gyllenhaal were an item for a couple of years

After her divorce, Witherspoon rebounded quickly with Jake Gyllenhaal. The pair were seen everywhere together for a while, but they weren’t built to last long-term. Ultimately, they dated from 2007 to 2009. There is no explanation for why they parted ways.

The following year, Gyllenhaal briefly dated Taylor Swift, and she has written about the ill-fated romance ever since. In her song “All Too Well,” she quips about a past lover whose new love interests remain young; she sings, “And I was never good at telling jokes / But the punchline goes: ‘I’ll get older, but your lovers stay my age.” The lyric hints at Gyllenhaal’s penchant for much younger women.

She went on to marry Jim Toth

It didn’t take long for Jake Gyllenhaal or Reese Witherspoon to get over their relationship. Around the time Gyllenhaal was romancing a much younger Taylor Swift, Witherspoon was falling for talent agent Jim Toth. In 2010, Witherspoon and Toth made their romance official. They married the following year.  

Things continued to move quickly, with the duo welcoming a son together in 2012. Everything seemed to be going exceptionally well. The pair rarely made headlines and seemed to work well as a couple for more than a decade. In a shocking twist, however, they announced their plans to split in 2023. It appears that the breakup was amicable, with the couple citing “growing apart” as the primary reason for their separation. They remain commited coparents, though.