Reese Witherspoon's 20-Year Trauma Amid New Romance

While Reese Witherspoon’s romance with German financier Oliver Haarmann is heating up, could there be the possibility of wedding bells in her future?

The Oscar-winner, 49, began dating the hunky billionaire, 57, last year following her shock split in 2023 from Jim Toth, her husband of 12 years.

Her divorce from the former Creative Artists Agency bigwig, 54, came 17 years after the end of her first marriage to Cruel Intentions co-star Ryan Phillippe, 50, in 2006.

While she and Toth reportedly divided their marital assets — including their production company, Hello Sunshine — according to their prenup, Witherspoon’s split with Phillippe wasn’t as simple.

As a result, insiders say Witherspoon — who boasts a net worth of over $400 million — isn’t interested in tying the knot for a third time.

‘Although she’s very much in love with Oliver, Reese isn’t dying to get married again after two costly divorces,’ a source exclusively told the Daily Mail.

‘She’s learned a lot from her last two marriages, especially her first which was without a prenuptial agreement.’

While Reese Witherspoon’s (pictured) romance with German financier Oliver Haarmann is heating up, an insider tells the Daily Mail that the star is in no rush to get married

The Oscar-winner, 49, began dating the hunky billionaire, 57, last year and they were caught packing on the PDA in Saint-Tropez over the weekend (pictured)

The source said that Witherspoon ‘loves’ that Haarmann (pictured) is successful in his own right

The insider says that the Legally Blonde star ‘loves’ that Haarmann — who is believed to be worth $440 million with a reported $10 billion in assets under management — is a self-made success with ‘significant assets of his own.’

‘She feels very safe with him and doesn’t feel the need to take that extra step of tying the knot,’ they said.

‘At her heart, Reese is a really savvy businesswoman now and a mogul in her own right, and marriage isn’t a priority for her.’

The Daily Mail has reached out to Witherspoon’s representatives for comment.

While there may not be a ring in the actress’ future, the couple have not shied away from public displays of affection. In photos obtained by the Daily Mail this week, the lovebirds were spotted packing on the PDA aboard a luxury yacht while on a romantic getaway in Saint-Tropez.

Their romance was first confirmed by the Daily Mail in July 2024, nearly a year after Witherspoon and Toth, who share 12-year-old son Tennessee, finalized their divorce.

Witherspoon was the one who filed for divorce in April 2023, just a week after announcing the end of their marriage on social media — just days after the couple’s 12th wedding anniversary.

‘It is with a great deal of care and consideration that we have made the difficult decision to divorce,’ the statement read, in part.

‘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,’ it continued.

‘Our biggest priority is our son and our entire family as we navigate this next chapter.

In her divorce documents, Witherspoon cited irreconcilable differences as the reason behind their breakup.

The documents also revealed that the couple had agreed to a prenuptial agreement in March 2011 just before their intimate Ojai, California wedding. Witherspoon indicated in her divorce filing that the contract was valid, ‘providing “adequate and sufficient provisions” for their assets and debts,’ according to TMZ.

The divorce was finalized four months later in August 2023, when the former couple reached a marital dissolution agreement and signed off on a parenting plan for their only child.

Witherspoon split from her husband of 12 years, Jim Toth, in 2023 (pictured: the couple in 2017)

Her first marriage to Cruel Intentions co-star Ryan Phillippe (pictured) came to an end in 2006 with no prenuptial agreement in place

Witherspoon is a proud mom of three. She shares daughter Ava (left), 25, and son Deacon (right), 21, with ex Phillippe. She welcomed her youngest son Tennessee (center), 12, during her marriage to Toth

While Witherspoon was reportedly ‘upset’ over the end of her marriage to Toth, she was no stranger to the difficulties of divorce.

In October 2006, Witherspoon’s marriage to Phillippe came to an end amid rumors of infidelity on Phillippe’s part, accusations he has denied.

The actors, who met two years before shooting the 1999 cult classic, were married for seven years and welcomed two children — daughter Ava, 25, and son Deacon, 21.

‘We are saddened to announce that Reese & Ryan have decided to formally separate. They remain committed to their family and we ask that you please respect their privacy and the safety of their children at this time,’ the pair said in a statement to TMZ.

Witherspoon, who did not sign a prenuptial agreement before marrying Phillippe, filed for divorce one month after the announcement, citing ‘irreconcilable differences’ as the reason for their shock split.

At the time of their marriage, Witherspoon was still an up-and-coming actress while Phillippe had already earned Hollywood heartthrob status after starring in the 1997 blockbuster slasher I Know What You Did Last Summer.

By the time they divorced in 2006, Witherspoon’s star power had greatly eclipsed Phillippe’s as she achieved A-list status for her work in Legally Blonde (2001) and her Oscar-winning role in the Johnny Cash biopic Walk The Line (2005).

Witherspoon was reportedly earning ‘at least $20 million per film’ while her then-husband Phillippe was earning ‘about $2.5 million per movie’ at the time of their divorce, according to ABC News.

The actress’ success sparked rumors of alleged tensions between her and Phillippe over their reported pay disparity.

Phillippe raised eyebrows at the 74th Academy Awards when he made a snide remark about Witherspoon ‘[making] more’ than him while he and his then-wife were presenting on stage together at the annual awards ceremony in 2002.

‘You make more than I do. Go ahead,’ Phillippe told Witherspoon after she asked to read out the winner’s name.

Witherspoon addressed the incident over a decade later during a 2020 appearance on the HFPA in Conversation podcast, where she admitted to being ‘flummoxed’ by her ex’s remark.

‘I forgot that ever happened. He did say that, and no, it wasn’t scripted. He didn’t tell me he was going to say that before it happened on air,’ she said.

Witherspoon was reportedly earning ‘at least $20 million per film’ while her then-husband Phillippe was earning ‘about $2.5 million per movie’ at the time of their 2006 divorce, according to ABC News

At the time of her split from Toth, a source told PEOPLE that Witherspoon ‘never saw herself getting another divorce,’ so she was still ‘disappointed’ by the way things panned out; the exes seen in 2020

With no prenup in place and the pair both residing in California at the time of their split, Witherspoon’s fortune likely took a hit as state law requires that earnings made during the marriage be divided 50/50.

The couple officially finalized their divorce in June 2008 and agreed to joint custody of their two children. Details of their settlement are unknown.

Witherspoon admitted in a 2014 interview with 60 Minutes that her brain was ‘scrambled eggs’ in the years following her divorce from Phillippe, who also previously described that period as the ‘worst time of [his] life.’

‘Phew, that was a tough year that followed. I got divorced the next year and I spent a few years just trying to feel better,’ Witherspoon said at the time. ‘You know, you can’t really be very creative when you feel like your brain is scrambled eggs.’

She said she also felt like she was ‘floundering career-wise’ despite being a recent Oscar-winner.

Witherspoon appeared to be in a much stronger place — both personally and professionally — in the aftermath of her 2023 divorce from Toth.

However, a source told PEOPLE at the time that Witherspoon ‘never saw herself getting another divorce,’ so she was still ‘disappointed’ by the way things panned out.

Her new beau Haarmann, however, has also gone through a divorce of his own.

The businessman — a Harvard Business School graduate and the founder of the private equity firm Searchlight Capital Partners — was previously married to businesswoman Mala Gaonkar, 55, with whom he shares two sons.