Reese Witherspoon Steps Out for Date with Oliver Haarmann Wearing Hat That Has a Sweet Nod to New Relationship

Multiple sources confirmed last month that Reese Witherspoon and the financier had moved from friends to dating

Reese Witherspoon is repping Oliver Haarmann's team.

The actress-producer, 48, wore a hat emblazoned with the logo for the New York Islanders, the NHL team Haarmann is a minority owner of, as she and the financier stepped out for a date in New York City on Tuesday, Oct. 1.

The duo were later joined by Witherspoon's son Deacon Phillippe, 20, to dine at Cafe Cluny in Manhattan's West Village neighborhood.

Multiple sources confirmed to PEOPLE last month that Witherspoon and Haarmaan had moved from friends to dating after they were spotted in N.Y.C. together, marking at least the second time in little over a month.

"They’re friends and it’s just casual," a source said of the pair's romance at the time.

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Related: Reese Witherspoon Spotted Out to Dinner with Financier Oliver Haarmann, Source Says They're 'Friends'

Witherspoon and Haarmann, who is also a founding partner of Searchlight Capital, were previously photographed in the Big Apple on July 30.

A source told PEOPLE at the time that Witherspoon and Haarmann were "friends," while another insider said the Sweet Home Alabama actress was "taking things slow when it comes to dating."

"She enjoys it but doesn't want it to be a big focus. She's busy with work and her son," said the source. "These are her biggest priorities."

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Related: Reese Witherspoon and Jim Toth's Relationship Timeline

News of Witherspoon's relationship with Haarmaan comes over a year after she and ex-husband Jim Toth announced their divorce in March 2023, after nearly 12 years of marriage. They settled their divorce by that August.

The Hello Sunshine founder shares one child with talent agent Toth, 54: son Tennessee, 12. Witherspoon also shares two kids with her first husband, Ryan Phillippe: daughter Ava Phillippe, 25, and son Deacon.

Haarmann is a graduate of Brown University and Harvard University, the latter of which he earned a master’s in business administration from, per his LinkedIn. He started his career at KKR, a global investment firm in London, before leaving to found Searchlight Capital Partners, a private equity firm, in 2010.

The financier has continued his role as a partner where he works with his two cofounders to oversee the firm’s activities and portfolio, per his bio on their website.

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