Rachael Leigh Cook’s Dating History: '90s Stars, Film Producers and More

Relive Rachael Leigh Cook’s most high-profile relationships from ex-husband Daniel Gillies to Kevin Mann and more — details

Love and life in the Fastlane! Rachael Leigh Cook has been linked to many high-profile celebrities throughout her career, especially when she was a rising star in the ’90s.

The actress made a name for herself in Hollywood with her 1995 debut as Mary Anne in The Baby-Sitters Club. She went on to play Becky Thatcher in Tom and Huck before landing the role of Laney Boggs in 1999’s She’s All That.

As her career skyrocketed to the top, Cook became a magnet for equally as successful men in the entertainment industry. Her former flames include Shane West, Rider Strong and Ryan Reynolds.

After settling down with now ex-husband, Daniel Gillies, in the early 2000s, Cook revealed that she had to do some inner reflection in order to make their marriage work for more than a decade.

“Something I need to learn myself is it’s a wonderful thing to be self-sufficient but it’s also good to be actively vulnerable so your partner can feel needed as well,” she exclusively told Us Weekly in January 2018. “That’s an important part of a partnership because it defines their role as your rock in this life. It’s something that I need to get a little bit better at.”

Cook’s marriage came to an end after nearly 15 years in 2019, but the Love, Guaranteed star didn’t stop looking for love. In fact, the actress exclusively told Us in August 2020 that she may have found her perfect match in Haven Entertainment cofounder Kevin Mann.

“He’s really great. I did good, if I do say so. Definitely hitting out of my league there,” she said at the time. “I met someone really nice, and I adore him. He’s fantastic.”

The Perception alum expanded on her romance with Mann, telling Entertainment Tonight in September 2020 that she “loves his perfect heat” and his overall personality.

“He’s magic. He’s a producer. He has incredible taste. He’s the greatest guy,” she gushed. “He’s fine with working really hard and doing great things, and he does so much for other people. And then he will watch unlimited seasons of 90 Day Fiancé with me.”

Despite being happy with the film producer, Cook revealed that her career momentum is what continues to drive her.

“I’m really putting my energy and myself forward and not being afraid to say, ‘You know what? I’ve seen some things and, yeah, I do know some things, and maybe I do have something to say that you would want to hear,'” she explained. “[I’m] just feeling better and better about putting that out there. I look forward to being increasingly creative, working hard behind the camera as well as in front, and diversifying quite a bit.”

Scroll down to relive Cook’s star-studded relationship history: