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EXCLUSIVE: Reese Witherspoon 'Planning Wedding Trial-Run' With Oliver Haarmann After Being Burned by 2 Failed Marriages

reese witherspoon planning wedding trial run oliver haarmann  marriages
Source: THE NEWS INTERNATIONAL

Reese Witherspoon is planning a wedding trial run with Oliver Haarmann after her two failed marriages.

June 18 2025, Published 6:00 a.m. ET

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Lovestruck Reese Witherspoon has fallen head over heels for financier Oliver Haarmann – but after two failed marriages, the cautious cutie wants to put their romance to the test by moving in together before tying the knot, RadarOnline.com can reveal.

According to insiders, The Morning Show star, 49, is on the fast track to cohabitating with the 57-year-old New York-based businessman and likening the future arrangement to a trial marriage to assess their long-term compatibility.

In March, the lovebirds reportedly checked out a posh Big Apple apartment in a new building designed by famed architect Robert A.M. Stern.

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reese witherspoon planning wedding trial run oliver haarmann  marriages
Source: SEARCHLIGHT CAPITAL; MEGA

Ryan Phillippe's past betrayal still lingers, pushing Witherspoon to treat her romance with Oliver Haarmann as a 'trial marriage.'

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"Reese is telling pals she's in love and she's found a great guy and talking marriage already, but she's taking their advice to take it slow," an insider confided.

The bubbly Legally Blonde beauty was first linked to Haarmann in July of last year.

"She's not going to rush into matrimony. They haven't even been dating for a year, but she sees no problem living together," the insider added.

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reese witherspoon planning wedding trial run oliver haarmann  marriages
Source: MEGA

Jim Toth's downfall also left Witherspoon wary.

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They also said: "She's hoping that sharing the same space and seeing Oliver on a regular basis will prove that her feelings for him are exactly right – and that he truly is the man she wants to spend the rest of her life with."

The longtime rom-com babe has had rotten luck with real-life happily-ever-afters.

She met first husband Ryan Phillippe at her 21st birthday party in 1997. The Cruel Intentions costars got hitched in 1999. But after seven years and two kids – daughter Ava, now 25, and son Deacon, 21 – they split amid rumors of Philippe’s infidelity.

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reese witherspoon planning wedding trial run oliver haarmann  marriages
Source: MAIL ONLINE/BLOOMBERG/GETTY IMAGES; MEGA

Robert A.M. Stern's luxe New York high-rise might soon host Witherspoon and Haarmann's 'living-together test run' before wedding bells ring.

Reese took the plunge a second time with then-CAA talent agent Jim Toth in 2011.

According to sources, she thought she'd found "the one," but that marriage also crashed and burned after 12 years and one son, Tennessee, 12.

As RadarOnline.com reported at the time, sources said Witherspoon's huge success as a star, producer and business whiz far outshined Toth's struggling career after he left his talent agent job for the failed mobile-first video service Quibi.

Our insider added: "Reese has been on the marriage merry-go-round twice already, so she's giving herself a reality check where Oliver is concerned.

"She thinks living together will be fun. If it doesn't work out, one of them moves out – easy peasy. Though she's pretty confident that won’t happen."

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