Before Blake Lively: Inside Ryan Reynolds' Rumored Fling With Rachael Leigh Cook

It's no secret that Ryan Reynolds had been through his fair share of relationships before he eventually struck gold and found his perfect match in Blake Lively. Between his marriage to Lively and Scarlett Johansson, his engagement to Alanis Morissette, and his rumored romance with Sandra Bullock (remember that?), it's easy to forget that he also dated Hallmark star Rachael Leigh Cook at one point in time. The truth about Reynolds and Cook's romance is that it was over almost as soon as it began. They reportedly crossed paths in 2001, just as Cook was preparing to leave for England to shoot scenes for "Blow Dry." Determined to woo her, Reynolds put his own filming schedule on hold and arranged a trip to London to surprise Cook. But the romance faded soon after, and by 2002, Reynolds, as we all know, had already moved on with Morissette. 

Unfortunately for us curious folks, neither the "Deadpool" star nor Cook (who was famous for starring in the '90s flicks "She's All That" and "The Baby-Sitters Club") has said anything about their romantic past. But back in 2005, Cook got candid about her relationships after saying "I do" with "The Vampire Diaries" actor Daniel Gillies, to whom she'd stay married until 2021. "I did my share of dating," Cook said in an interview with InStyle (via People). "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."

Unlike Ryan Reynolds, who has been happily married to Blake Lively since 2012, his ex-girlfriend Rachael Leigh Cook hasn't been as lucky in love. In 2019, fans were shocked after she and Daniel Gillies revealed they were separating after 15 years of marriage through a joint statement. Thankfully, the split was cordial; the two agreed on shared legal and physical custody of their children, Charlotte and Theodore, and remained close. "You know, 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," Cook told ET regarding their split. "But I don't know. I still love him to death." She even said of her ex, "He's an amazing person and I still consider him my very best friend and we'll make it one way or another."

Since then, Cook has dipped her toes back into the dating pool in hopes of finding a second chance at love. In 2021, months after finalizing her divorce from Gillies, she went public with her relationship with producer Kevin Mann, though that eventually fizzled out. After Mann, she was later linked to actor Brandon Routh when photos of them holding hands at a movie date were published by news outlets. The pair confirmed their romance by making their red carpet debut at the 2026 premiere of "Slanted" in Los Angeles.

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."