It’s no secret that Ryan Reynolds had been through his fair share of relationships before he finally 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. 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 travel to England to shoot scenes for “Blow Dry.” Determined to woo her, Reynolds put his own film schedule on hold and arranged a trip to London to surprise Cook. But the romance faded soon after, and in 2002, Reynolds, as we all know, had already moved on with Morissette.
Unfortunately for us nosy people, neither the “Deadpool” star nor Cook (who was famous for starring in ’90s films “She’s All That” and “The Baby-Sitters Club”) has spoken out about their romantic past. But back in 2005, Cook got candid about her relationships after saying “I do” to “The Vampire Diaries” actor Daniel Gillies, to whom she would remain 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’s over’. But I’m so glad because I’ve never been good at that.”
Inside Rachael Leigh Cook’s love life
In contrast to Ryan Reynolds, who has been happily married to Blake Lively since 2012, his ex-girlfriend Rachael Leigh Cook has not been so lucky in love. In 2019, fans were shocked after she and Daniel Gillies revealed that they were splitting up after 15 years of marriage through a joint declaration. Fortunately, the split was cordial; the two agreed to 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 it’s hard,” Cook shared A about their split. “But I don’t know. I still love him to death.” She even said of her ex: “He’s a great person and I still consider him my very best friend and we’ll work it out somehow.”
Since then, Cook has been dipping her toes back into the dating pool, hoping to find another chance at love. In 2021, months after finalizing her divorce from Gillies, she went public with her relationship with producer Kevin Mann, although it eventually stalled. After Mann, she was later linked to actor Brandon Routh when photos of them holding hands on a movie date were published by news outlets. The couple confirmed their romance by making their red carpet debut at the 2026 premiere of “Slanted” in Los Angeles.
Despite her separation from Gillies, Cook said she hasn’t ruled out marriage and would still consider walking down the aisle again if the right person came along. Although, as the mother-of-two told People in 2022, “(I) will be a little more cautious about making that decision because I have kids involved and stuff in my life now.” But then she added, “I wouldn’t say no.”
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