Ryan Reynolds, best known for slicing villains and fourth walls as Deadpool (and trying to forget his Green Lantern glow-up), has not just battled bad guys- he has also navigated the drama of celebrity love. Recently, he found himself headline-adjacent, thanks to wife, Blake Lively’s rumored feud with Justin Baldoni. But, Lively is not his only epic romance—Reynolds clearly skipped the one true love memo. So, let us rewind the rom-com reel and peek at his star-studded dating history.

Ryan Reynolds' lineup of ex-lover history might just rival Ye, formerly Kanye West's epic saga of feuds and fallout—let us dive into the drama-packed archives.

Before Ryan Reynolds became the wisecracking Deadpool, he briefly dated Melissa Joan Hart after they met on the set of Sabrina the Teenage Witch in 1996. Hart later revealed their fling was sweet and passionate, describing him as “adorable” and “a really nice guy.”

However, the romance fizzled quickly—she had a boyfriend at the time and chose to stay loyal, leaving Reynolds lovestruck and broomless.

Long before Ryan Reynolds was headlining blockbusters, he starred in Two Guys and a Girl, where he reportedly shared an eight-month fling with co-star Traylor Howard. Though never confirmed, their on-set spark was widely buzzed about.

Reynolds later gushed in 2022 that the sitcom was among his favorite gigs, and revealed he still keeps in touch with Howard and Nathan Fillion.

Back in 1999, Ryan Reynolds and 3rd Rock from the Sun star Kristen Johnston shared a blink-and-you-will-miss-it romance. The duo even attended The Green Mile premiere together before parting ways months later.

Years down the line, Johnston described Reynolds as “lovely” and “a great guy”—clearly no hard feelings. Just a sitcom-to-sitcom love story that fizzled faster than a punchline.

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In 2001, Ryan Reynolds reportedly channeled his inner rom-com hero and jetted off to the UK to surprise Rachael Leigh Cook on the Blow Dry set. Fresh off a split with Kristen Johnston, Reynolds reportedly swooped in like a Canadian Cupid. Though whispers claimed the duo dated for a year, the stars never spilled the tea, leaving fans with a classic Hollywood maybe.

Ryan Reynolds and Alanis Morissette were once Hollywood’s surprise power duo, who first locked eyes at Drew Barrymore’s birthday bash in 2002. Sparks flew hard and fast—they got engaged in 2004! She called their chemistry the "perfect combination of compatibility and incompatibility,” but the romance burned bright and fizzled by 2007.

  Morissette later confessed love hit her like a truck, too intense, too often, and exhausting.

Back in 2007, Ryan Reynolds hit the romance fast-forward button with Scarlett Johansson. The duo wed in 2008, blinked, and were done by 2010. So under the radar was their union, even Gwyneth Paltrow forgot it happened.

Johansson had to jog her memory on The Goop podcast in 2023, casually confirming she was married to Deadpool before she met Iron Man. Hollywood amnesia, anyone?

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After The Proposal set tongues wagging, 2011 saw sparks fly—or so people hoped—between Ryan Reynolds and Sandra Bullock. Fresh out of his marriage, Reynolds was linked to Bullock, but she quickly shut the rumors down with sass at the Golden Globes.

Turns out, their flirty film vibes were just top-tier acting. Bullock made it clear: Reynolds was strictly bestie zone, not an after-dark friend.

After his high-profile split, Ryan Reynolds reportedly took a scenic detour into rebound territory with German model Agnes Fischer in 2011. Best known for popping up in Valkyrie and charming her way through a few European films, Fischer and Reynolds were spotted together, setting the gossip mill ablaze.

Was it love or just another post-divorce plot twist? Either way—10/10 for drama!

Back in 2011, Ryan Reynolds and Charlize Theron reportedly stirred up some summer heat after mutual pals played Cupid. Having lived just doors apart and known each other for years, sparks reportedly flew fast—then fizzled out just as quick. By August, their schedules hijacked the fling, and the two called it quits before it even got Coachella-level official.

Ryan Reynolds and Blake Lively turned their friendship into a full-blown fairy tale in 2011, tying the knot the next year. Sparks flew faster than a rom-com montage, and over a decade later, the duo is still going strong.

With daughters James Reynolds, Inez Reynolds, Betty Reynolds, and baby Olin Reynolds—plus a curveball claim from a different Natalie Reynolds—this Hollywood family stays entertaining on and off-screen.

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What are your thoughts on Ryan Reynolds’ whirlwind dating history before Blake Lively? Let us know in the comments below.