From Hollywood Heartthrobs to Enduring Love: The Untold Stories of Reese Witherspoon's A-List Romances

Reese Witherspoon has had her fair share of high-profile romances, but not all of them have had fairy tale endings. One of her most notable relationships was with Ryan Phillippe, whom she met at her 21st birthday party in 1997. The pair went on to portray love interests in the film Cruel Intentions, released in 1999. While the movie may have enchanted fans, Witherspoon revealed during an interview with Andy Cohen that their children, Ava and Deacon, had no interest in seeing their parents' on-screen romance.

"They find it really strange to witness their dad and I engaging in sexual activity. It's just such a peculiar experience," she shared with the Bravo host back in 2015.

Regarding their separation, The Shooter star reminisced about strolling through Manhattan with Witherspoon and their kids after their divorce. (They ended their marriage in 2006 after being together for five years, and their official separation was finalized in 2008.)

It was a humorous moment for us as we reminisced about shooting a significant amount of Cruel Intentions in this location. The kids were amazed to realize that we filmed a movie here before they were even conceived. During the interview with Huffington Post Live, he mentioned that both of them were in a happy and content space in their relationship at that time.

Nevertheless, the divorce had a lasting impact on Witherspoon.

"I spent several years in a relentless pursuit of finding solace," the winner of an Academy Award recounted during an interview with 60 Minutes in 2014. "One's creativity suffers greatly when the mind feels utterly disoriented. My professional trajectory was aimless as I was merely churning out projects without any genuine passion. It became evident that the audiences were not connecting with anything I produced."

Nevertheless, a new chapter unfolded with the entrance of publicist Jim Toth in her life, leading to their marriage in 2011. Witherspoon and Toth joyfully welcomed their son, Tennessee, the subsequent year.

Toth and Witherspoon, known for their highly-publicized arrest in 2013, where Toth was charged with a DUI and Witherspoon with disorderly conduct, had a quiet and long-lasting romance for over ten years. However, in March 2023, the couple revealed their split through a statement on social media.

"We have made the challenging choice to end our marriage with utmost consideration and care," the estranged couple shared. "Although we have shared many incredible years together, we are now moving forward with immense love, kindness, and mutual respect for all that we have built."

The ex-partners stated: "Our utmost concern lies with our son and our entire family as we move forward in this new phase. Dealing with such matters is never simple and they hold great personal significance. We sincerely appreciate everyone's consideration for our family's privacy during this period."

Continue scrolling to discover Witherspoon's dating journey over the years:

Credit: Image Press Agency/NurPhoto/Shutterstock

Reese Witherspoon’s Dating History: Ryan Phillippe, Jake Gyllenhaal, Jim Toth and More of Her A-List Romances

What, like it’s hard? Reese Witherspoon has romanced multiple A-listers throughout her time in the spotlight, but not all of her relationships have had happily ever afters.

In 1997, Ryan Phillippe and Reese Witherspoon first met at her 21st birthday party. They later portrayed love interests in the film Cruel Intentions released in 1999. Although the movie captivated fans with their characters' romance, Witherspoon revealed to Andy Cohen in 2015 that their children, Ava (born in 1999) and Deacon (born in 2003), had no interest in watching the film. Their reaction to witnessing their parents engaged in intimate scenes was described as "weird."

The Shooter star, on his part, remembered taking a stroll in Manhattan with Witherspoon and their children after their divorce. (The couple ended their five-year marriage in 2006 and officially divorced in 2008.)

"It was amusing - we were reminiscing because we filmed a lot of Cruel Intentions [here]... and [the kids] were amazed that we were shooting a movie there before they even existed," he shared with Huffington Post Live at that time, emphasizing that they were currently in a "wonderful place" as former partners.

The divorce, however, had a significant impact on Witherspoon for an extended period.

"I spent several years attempting to regain a sense of well-being," the 2014 interview with 60 Minutes revealed. "When your mind feels chaotic, creativity becomes a challenge. I was struggling professionally because I wasn't pursuing projects that ignited my passion; I was merely going through the motions. It became evident that audiences were not connecting with any of my work."

However, she quickly moved on with her publicist Jim Toth, whom she married in 2011. They later had a son named Tennessee in the subsequent year.

Apart from a widely-publicized incident in 2013, where Toth was arrested for a DUI and Witherspoon was handcuffed for disorderly conduct, the Wild actress and her husband had a quiet and private relationship for over ten years. Unfortunately, in March 2023, the couple made the announcement of their separation.

"We have reached a tough resolution, fully aware of the significance, as we announce our decision to divorce on social media," shared the estranged couple. "Despite the challenges, we cherish the incredible moments we have shared and intend to proceed with profound affection, benevolence, and reverence for the life we have built together."

The former partners further stated, "Our utmost concern lies in the wellbeing of our son and the entirety of our family as we embark on this new phase. Such matters are invariably difficult and deeply intimate. We sincerely thank everyone for their understanding and consideration of our family's need for privacy during this period."

Keep scrolling for Witherspoon’s dating history throughout the years:

Credit: Shutterstock (2)

Jeremy Sisto

Before her relationship with Phillippe, Witherspoon was previously in a well-known '90s couple when she dated Clueless star Sisto.

"Reese was my first girlfriend who was an actress," the actor from Waitress recalled during a 2015 Reddit Ask Me Anything (AMA), mentioning that they connected while working on a television movie in 1992. "We were in a long-distance relationship for quite some time," he revealed, expressing his enthusiasm by saying, "I was really into her."

Credit: London Entertainment/Shutterstock

Ryan Phillippe

Sparks erupted when the actor from I Know What You Did Last Summer crossed paths with Witherspoon at her 21st birthday celebration in 1997. The following years were a whirlwind of happiness for the then-couple, who not only co-starred in the movie Cruel Intentions in 1999, but also got engaged, tied the knot, and joyfully welcomed their firstborn, their daughter Ava. Deacon became a part of their family four years later. Seven years after their marriage, the duo separated amidst speculations that Phillippe was unfaithful to the Man in the Moon actress with Abbie Cornish, whom he subsequently started dating. (The Locksmith actor vehemently denied the accusations of infidelity.)

“We regretfully inform you that Reese and Ryan have made the difficult decision to officially separate,” stated a representative for the actors. “They continue to prioritize their family and kindly request that you honor their privacy and safeguard the well-being of their children during this period.” Their divorce was ultimately concluded in 2008. Despite the personal challenges they faced, Witherspoon and Phillippe remain steadfast in their commitment to co-parent their children.

Credit: Sandro Pace/AP/Shutterstock

Jake Gyllenhaal

Witherspoon and Gyllenhaal started a romantic relationship in 2006 during the production of the film Rendition. However, their three-year relationship came to an end in 2009 without any significant reasons, according to an exclusive source from Us. "No one cheated," assured the source. "There was no drama."

Credit: John Salangsang/Invision/AP/Shutterstock

Jim Toth

One year after ending her relationship with Gyllenhaal, Witherspoon started dating Toth. Their relationship advanced rapidly, and they got married in 2011. They welcomed their son Tennessee just one year later.

However, in 2013, Witherspoon made headlines for her unusual behavior when she was arrested for disorderly conduct, and Toth was arrested for a DUI. According to the police report at the time, the actress asked the police officer if he recognized her name.

"I responded, 'No, your name is not necessary for me to know,' the officer recounted, according to Variety. The report mentioned that "Mrs. Witherspoon asserted, 'You're about to discover my identity.'" The star of Your Place or Mine later expressed remorse for her actions in a statement to Us.

"I clearly had consumed one too many drinks, and I feel immense embarrassment for the remarks I made. While it was an alarming situation, and I was worried for my husband's safety, I understand that it does not excuse my behavior. I displayed disrespect towards the officer who was simply carrying out his duties. The language I used that evening in no way reflects my true self. I hold nothing but admiration for law enforcement, and I sincerely apologize for my conduct."

Toth, the driver of the car, was convicted and given a sentence of community service, one year of probation, and required to attend an alcohol education program after pleading guilty. Witherspoon, on the other hand, pled no contest to disorderly conduct and was fined. Despite enjoying positive media attention for several years, celebrating anniversaries and bonding with their children, Toth and Witherspoon made the public announcement of their divorce in March 2023.

"We have made the difficult decision to divorce with utmost care and thoughtfulness," they shared on social media. "Throughout the many beautiful years we spent together, we now move forward with profound love, kindness, and mutual respect for all that we have built."

The couple further expressed, "Our highest priority remains our son and our entire family as we venture into this new chapter. Such matters are always challenging and deeply personal. We sincerely thank everyone for respecting our family's privacy during this time."

Witherspoon and Toth finalized their divorce in August 2023. The duo signed a marriage dissolution agreement and agreed to a parenting plan for son Tennessee.