A Look Back at Ryan Reynolds’ Alleged Past Romance with Rachael Leigh Cook Before Blake Lively

Ryan Reynolds has navigated through a series of high-profile relationships before finding lasting happiness with Blake Lively. His romantic history includes a marriage to Scarlett Johansson, an engagement to Alanis Morissette, and rumors of a fling with Sandra Bullock. However, one often overlooked chapter in Reynolds’ dating life was his brief romance with Hallmark star Rachael Leigh Cook. Their relationship began in 2001, around the time Cook was set to depart to England for her role in the film “Blow Dry.” In an effort to win her over, Reynolds paused his own work commitments to make a surprise visit to London. Despite this grand gesture, their relationship quickly fizzled, and by 2002, Reynolds had moved on to his next relationship with Morissette.

Both Reynolds and Cook have kept tight-lipped about their short-lived romance. Known for her roles in ’90s classics like “She’s All That” and “The Baby-Sitters Club,” Cook provided a rare glimpse into her relationship history during a 2005 interview with InStyle, after marrying Daniel Gillies from “The Vampire Diaries.” Reflecting on her past after tying the knot, Cook admitted, “I did my share of dating,” as reported by People. She humorously noted the gravity of marriage with, “I remember looking in the mirror one day after we got married and seeing my ring and thinking, ‘Wow, the party is over.’ But I’m so glad because I was never good at that.”

While Reynolds enjoys a seemingly blissful marriage with Lively since 2012, Rachael Leigh Cook’s romantic journey has faced more turbulence. The actress and her husband Daniel Gillies shocked fans in 2019 with the announcement of their separation after 15 years of marriage, releasing a joint statement that emphasized their amicable split. The couple agreed to share custody of their children, Charlotte and Theodore, maintaining a close bond. In a conversation with ET, Cook reflected on their split, stating, “We got married when I was 24. I think we were just a little bit ahead of the curve, so it feels like we’re first, and that’s hard.” She fondly added, “I still love him to death,” and praised Gillies as “an amazing person” who remains her best friend.

Cook has since ventured back into the world of dating, optimistic about finding love anew. In 2021, following her divorce’s completion, she publicly began dating producer Kevin Mann, though that relationship eventually ended. She later sparked romance rumors with actor Brandon Routh when photos of them on a movie date surfaced. The duo confirmed their relationship by making a joint appearance on the red carpet at the 2026 premiere of “Slanted” in Los Angeles, cementing their status as a couple.

Despite her split from Gillies, Cook said she hasn’t ruled out marriage and would still consider walking down the aisle again should the right person come along. Although, as the mom-of-two told People in 2022, “[I] will be slightly more cautious in making that decision because I have kids involved and such in my life now.” But then, she added, “I wouldn’t say no.”