Reese and Jake Get Close

Five months after announcing her split from husband Ryan Phillippe, Reese Witherspoon seems to be wading back into the dating pool – with Jake Gyllenhaal, her costar in the upcoming CIA thriller Rendition.

Although the two have been careful to avoid the spotlight, they were spotted March 23 dining with two other couples at L.A.'s Il Sole. "They were cuddling," an observer tells PEOPLE in its new issue. "It looked very playful."

And now friends of both say the relationship extends beyond the occasional dinner. "In the last month, they've been spending a lot more time together," says a source close to Gyllenhaal, adding that the actor has even met up with Witherspoon, 31, and her kids – daughter Ava, 7, and son Deacon, 3 – in New York City. At 26, he is five years her junior, but "Jake really likes her and isn't at all concerned that she has two kids."

Gyllenhaal's rep had no comment.Witherspoon's rep did not return calls.

Still, Witherspoon isn't rushing into another high-profile Hollywood relationship, says a source close to the Oscar winner. "[Reese] is still very, very hurt by Ryan and it will take a long time to get over that," the source explains. "[But she and Jake] have a mutual interest. They are taking it slow and getting to know each other."

One common point may be their homebody lifestyles. Family-first Witherspoon routinely picks up her kids from school and takes Ava for mommy-and-me manicures. As for Gyllenhaal – who's uncle to sister Maggie's 6-month-old daughter Ramona and godfather to Heath Ledger's 17-month-old Matilda – he's "very into kids," says a source.

Although he dated nightlife-loving Kirsten Dunst for nearly two years, "Jake has never been about staying out late partying," the insider adds. "This is what he wants."

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