Reese Witherspoon Took a Major Step in Her Blossoming Relationship With Oliver Haarmann

Reese Witherspoon’s blossoming romance with Oliver Haarman might be kicking into high gear after the paparazzi captured a major step in their relationship. On Tuesday, Oct. 1, Witherspoon, her financier boyfriend, and her son, Deacon Phillippe, were spotted out to dinner at Cafe Cluny in New York City.

According to the Daily Mail, this was the “first time that Reese and Oliver have been seen enjoying an outing with one of her children.” That makes for quite a milestone in their relationship and could signal that things are getting serious between them. Witherspoon wore a camel-colored blazer with a matching baseball hat and black pants. Haarman looked more formal in a sports coat and a light blue button-down shirt. Phillippe dressed as any college student would: jeans, baseball cap, white T-shirt, and plaid flannel jacket. 

Witherspoon has been dating the German entrepreneur since the summer. Their first sighting came on July 30, but a People source emphasized that this was a casual relationship. They noted that the 48-year-old actress was merely “friends” with the 57-year-old businessman and that she “is taking things slow when it comes to dating.” The insider added, “She enjoys it but doesn’t want it to be a big focus. She’s busy with work and her son. These are her biggest priorities.”

However, the duo has been seen together more over the last few months, which might be an indication that this is not a casual romance. This would be her first major relationship after finalizing her divorce from her second husband, Jim Toth, in August 2023. She shares one son, Tennessee, 11, with Toth. She also shares her adult children Ava, 25, and Deacon, 20, with ex Ryan Phillippe. Haarman was formerly married to Mala Gaonkara, and they have two children. 

Witherspoon was quite open about her second divorce, telling Harper’s Bazaar last July, “To be able to talk to people directly about what’s going on in my life and just share it in the way that I share great professional experiences or personal experiences, it feels much more authentic to be able to say things in my own voice and not let somebody else control what’s happening,” she said. Even though it was a “vulnerable” time for her, she felt that her approach to heartbreak worked better for her the second time around — and it left Witherspoon open to love when she was ready.

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