Inside Ryan Reynolds' Relationship With Rachael Leigh Cook

Gen Z today might know actress Rachael Leigh Cook from her role as the mom in Netflix's "He's All That." But older generations know that Cook was once a household name, thanks to her roles in iconic films like "Josie and the Pussycats," "She's All That," and even "The Babysitter's Club" (via IMDb). Since then, Cook's been mostly out of the spotlight, taking on smaller film roles or appearing on television in "Psych" and "Titan Maximum."

Of course, given Cook's popularity, her love life was a subject of interest as well. As a '90s teen star, it makes perfect sense that Cook would date other teen stars as well (via Us Weekly). Amongst Cook's exes are Shane West ("Get Over It," "A Walk to Remember"), Rider Strong (who won hearts everywhere as the troubled Shawn in "Boy Meets World"), and Antonio Sabato Jr. ("Melrose Place," "Ally McBeal").

However, come 2001, Cook was off the market for a long while: That year, Cook began dating future "Vampire Diaries" actor Daniel Gillies, and three years later the two wed. Sadly, 17 years and two kids later, Cook and Gillies officially split.

But there's one early aughts Cook romance that might have slipped past your radar — her romance with "Deadpool" star Ryan Reynolds.

How Reynolds wooed Cook

It's true: The man you know and love from his roles in "The Proposal," "Definitely Maybe," and perhaps even "Just Friends," once dated Rachael Leigh Cook (via Us Weekly). While Reynolds has had plenty of other high profile relationships with Alanis Morisette, ex-wife Scarlett Johansson, and current wife Blake Lively, so it makes sense that his courtship with Cook might not have caused as much of a frenzy.

The two met in 2001. Although the two quickly connected, Cook had to then head to England, where she was filming the film "Blow Dry." Pulling a page out of the romantic comedies he would go on to star in, Reynolds flew across the world to surprise her — even getting out his own film obligations to do so.

The two dated for a year, and while it's not clear why it didn't work out between them, Cook went on to meet and marry Gillies, and Reynolds, for his part, met Alanis Morissette at Drew Barrymore's birthday in 2002 (via CheatSheet).

Today, Cook is now dating film producer Kevin Mann, while Reynolds remains wed to Blake Lively — but hey, they'll always have England.