Reese Witherspoon Boyfriends 2021: Who Is Reese Dating Now?

Reese Witherspoon, born March 22, 1976, in New Orleans, Louisiana is a beloved and award-winning actress, especially known for her role as Elle Woods in the Legally Blonde film franchise. Witherspoon has been in the acting circuit since the early 1990s. Throughout her acting career, she has been romantically linked to a number of fellow well-known actors.

Keep reading for a look into Reese Witherspoon’s dating history.

Jeremy Sisto (1992)

Jeremy Sisto arriving to screening of 'Break Point'


Reese and Jeremy met on the set of the television movie, Desperate Choices: To Save My Child. The two were co-stars as Reese starred as Cassie Robbins, a young teenage girl suddenly diagnosed with leukemia and Jeremy starred as Josh Ryan. The then teenagers became close and eventually began dating after filming was finished. As most teenage relationships it was fairly brief, especially since it was primarily long distance as Reese was away filming for A Far Off Place (1993) in Namibia and Zimbabwe. Back in the early 90s, cross-continental communication was not nearly as accessible in comparison to that of today. That being said, just over two decades after the young couple separated Jeremy Sisto has briefly talked about his relationship with Reese Witherspoon and has revealed that Reese was his first actress girlfriend. As stated before, during the bulk of their romance Reese was away in south-central Africa where staying in touch with one another was quite difficult, thus causing the young couple to eventually end their brief relationship.

Chris O’Donnell (1993)

Actor Chris O'Donnell arriving to 2017 Teen Choice Awards


Subsequently after ending her relationship with her former Desperate Choices: To Save My Child co-star, Jeremy Sisto, rumors began to circulate about Witherspoon and O’Donnell dating after she accompanied him to a tribute party for the acclaimed actor, Al Pacino in 1993. Both Witherspoon and O’Donnell remained quiet about the alleged relationship. The rumors soon began to quiet and fade into the background.

Stephen Dorff (1993)

Actor Stephen Dorff at premiere of HBO's "True Detective"


Dorff and Witherspoon encountered one another two years before rumors of the S.F.W. co-stars dating began to arise. In 1991 the two young actors met at a night club in [location]. They would later on film the comedic film S.F.W. (1994) together. They were spotted together multiple times during this time. Neither Dorff or Witherspoon directly confirmed or denied the speculation of a relationship between the two co-stars.

Mark Wahlberg (1996 – 1997)

Still of young Mark Wahlberg and Reese Witherspoon from the film "Fear" swimming


In 1995 Witherspoon began filming for her part as Nicole Walker for the thriller Fear that was released in 1996; while on board for this film on of Witherspoon’s lead co-stars is Mark Wahlberg who stars as David McCall. The chemistry that was seen on the silver screen carried over into reality as rumors of Witherspoon and her then co-star Mark Wahlberg having a real-life romance began to travel through the grapevine. Neither Reese nor Mark confirmed or denied these rumors.

Ryan Phillipe (1997 – 2006)

Actress Reese Witherspoon and ex-husband Ryan Phillipe

Jody Cortes / WENN

The Cruel Intentions co-stars, Reese Witherspoon and Ryan Phillipe first met in 1997 during her 21st birthday celebration. They were taken by each other almost immediately and soon began dating. A year later the couple was engaged in December of 1998 and subsequently the young actors married in 1999 in a small ceremony. Phillipe and Witherspoon went on to have two children with one another- Ava Phillipe in 1999 and Deacon in 2003. The couple was married for seven years before Witherspoon filed for divorce in 2006. The relationship did not end bitterly as both actors remain on great terms with one another as they continue to raise and support their children together.

Jake Gyllenhaal (2007 – 2009)

Actress Reese Witherspoon holding hands with actor Jake Gyllenhaal at 2009 Coachella festival


Following her divorce from actor, Ryan Phillipe, Reese began dating actor Jake Gyllenhaal. The two became acquainted with each other as they were co-stars for the movie Rendition. Their relationship was as low-key as it was public as the couple was seen and photographed with one another on numerous occasions looking quite close and happy to be in each others’ presence. After two years, the relationship came to a quiet end in 2009 as both parties began to drift apart due to wanting different directions for the relationship.

Jim Toth (2010 – Present)

Reese began dating talent agent and co-head of Creative Artists Agency, Jim Toth in early 2010. By December of that same year, the couple announced their engagement and were married three months later in March of 2011. The following year, the couple welcomed their son Tennessee in September of 2012.

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