Inside Ryan Reynolds' Failed Relationships With Hollywood Stars

Ryan Reynolds and Blake Lively have one of the most adorable marriages in Hollywood, but the actor had quite a few failed relationships with other stars before he found his perfect match in the "Gossip Girl" actor. The pair began dating in 2011, by which time Reynolds had both a failed engagement (to Alanis Morrissette) and a divorce (from Scarlett Johansson) under his belt. In fact, Reynolds was married to Johansson when he and Lively met on the set of "Green Lantern" the year prior. Lively was similarly involved, so nothing happened between the pair until well after Reynolds' divorce. He even had a brief fling with another huge star in the small gap between Johansson and Lively.

In addition to the aforementioned relationships, Reynolds had a slew of other failed romances between the start of his acting career and his first marriage. This includes a few that did not make our list due to shoddy known details, like his supposed partnership with former co-star Traylor Howard or model Agnes Fischer, which both lack a clear timeline. Our list also does not include Sandra Bullock — who many assume Reynolds dated due to their intense chemistry — because both parties have denied there was ever a romance. Shippers on that particular love train will have to rely on "The Proposal" to live out their fantasies. 

Besides, there are more than enough defunct romances in Reynolds' history. Here is a look inside Ryan Reynolds' failed relationships with Hollywood stars over the years.

On its face, Ryan Reynolds and Kristen Johnston feel a bit like an odd coupling. Johnston is nearly a decade older than Reynolds, and she has always had a lowkey vibe — in contrast to the "Deadpool" actor's slightly thirstier approach to fame. Looking at this list, however, it is clear that Reynolds has no particular type. Given their shared goofiness, it feels fair to reason that a large part of the attraction between Johnston and Reynolds was humor. It is clear that a shared sense of humor is important to Reynolds, if only from looking at his marriage to Blake Lively. Fans have found much joy in observing Reynolds' interactions with his current wife, as he and Lively love to publicly roast one another in interviews and especially on social media.

But back to Johnston, who was busy earning Emmys for her work on "Third Rock From the Sun" when she met an up-and-coming Reynolds. He was also a TV star at the time, appearing on the ABC show "Two Guys and a Girl," co-starring another woman Reynolds supposedly dating, Traylor Howard. 

Though exact timelines are not known, Johnston and Reynolds were photographed together at a movie premiere in December 1999, which gives a rough sense of when they were together. The relationship was also confirmed by Johnston herself when she appeared on "Watch What Happens Live" in 2020. "It was so long ago I forgot," Johnston replied when asked about Reynolds. "But literally so nice. Great guy. Lovely."

Though there are fewer publicly available details about Ryan Reynolds' relationship with Rachael Leigh Cook than is ideal, Cook's popularity at the time they dated ensured we had at least some of the scoop. After all, while she may not be a household name for Gen Z, Cook was a huge deal in the late 1990s and early 2000s. A teen idol known for her work in films such as "The Baby-Sitters Club" and "Tom and Huck," Cook's career reached new heights when she appeared in the iconic 1998 movie "She's All That." She released five feature films in 2001, the year that she dated Reynolds, including the high-profile but ultimately unsuccessful "Josie and the Pussycats." In contrast, Reynolds only broke out in movies in the two or three years following his romance with Cook.

The early parts of this particular relationship seemed quite dreamy. It was not long after splitting from Kristen Johnston that Reynolds met Cook, and the pair sparked up a romance. And when Cook had to leave for England — where she was filming the movie "Blow Dry" — Reynolds dropped his acting commitments and flew across the pond to hang with his new beau. The grand surprise might read like a gesture pulled from a cheesy romantic comedy script, but it was enough for a real romance to bloom. The couple dated for roughly a year, which is not shabby at all for two 20-somethings in Hollywood.

Ryan Reynolds and Alanis Morissette might feel like yet another unlikely coupling, but the stars are both Canadian natives and have a very similar sensibility because of it. Morissette is also far funnier than she gets credit for, as anyone who recalls her parody of "My Humps" already knows — and surely Reynolds must have scholarly and spiritual characteristics in addition to the goofball ones. While Reynolds never walked down the aisle with the "Jagged Little Pill" singer, the pair genuinely seemed to balance each other well. "We have the perfect combination of compatibility and incompatibility that makes the relationship very passionate. It's perfect. I think it's about stretching each other," Morissette once told People.

Reynolds and Morissette first met at a February 2002 party thrown by mutual friend Drew Barrymore. They were not spotted in public together for a year thereafter, but things were obviously serious behind the scenes. The pair got engaged in June 2004, and they remained engaged for three years without ever setting a wedding date. "We feel like we're already married," Reynolds said in 2005 (via People). 

Alas, the marriage never came. Reynolds and Morissette broke up in June 2006, reunited the following month, then split again — this time for good — in February 2007. "Ryan Reynolds and Alanis Morissette have mutually decided to end their engagement. They remain close friends and continue to have the utmost love and admiration for each other," representatives for the couple said in a joint statement released to People.

Everyone was rooting for Ryan Reynolds and Scarlett Johansson when they were together but, looking back, the failure of their marriage was a blessing in disguise. Reynolds is now married to Blake Lively and — even though some have identified potential signs of trouble in the marriage — much of the concerns feel blown out of proportion and perhaps even due to envy. Reynolds and Lively appear to be happy together and have built a beautiful life with their four children. Similarly, after a second divorce (from Romain Dauriac, the father of her oldest daughter), Johansson seems to have found lasting love with "Saturday Night Live's" Colin Jost. That pair have been together since 2017, got married in 2020, and welcomed a child in 2021.

While marriage number three is working for Johansson, the star has blamed her first marriage's failure on her young age at the time. "I mean, the first time I got married I was 23 years old. I didn't really have an understanding of marriage," Johansson said in a 2019 Vanity Fair interview. "Maybe I kind of romanticized it, I think, in a way. It's a different part of my life now." 

Reynolds and Johansson were both fresh out of long-term relationships when they started dating in April 2007. They were engaged in May of the following year and married that September. While the actors separated in December 2010, they were technically married for close to three years, as the divorce was only finalized in July 2011.

Finally, let's get into the truth about Ryan Reynolds' relationship with Charlize Theron, which was brief and largely flew under the radar. Theron is the total package — incredibly gorgeous, undeniably talented, and uber-successful. Judging by interviews and media coverage, she is also a super cool chick with a good sense of humor, a down-to-earth vibe, and a deep love for her mother and her kids. But it is a sad fact of life that even the brightest shining stars have romantic failures, and Theron suffered one when Reynolds ended things after only a few months of dating. Despite having several famous exes of her own, Theron rarely flaunts her relationships so, unsurprisingly, little is known about her short fling with Reynolds.

In July 2011 — the same month Reynolds' divorce was finalized — Marie Claire UK reported that Reynolds and Theron had been secretly dating "for months." Therefore, this may have simply been a rebound for Reynolds and a chance to cleanse his palate of the sour taste of a failed marriage. For Theron, however, it may have been more than that. Us Weekly confirmed as much when they reported news of the breakup not long after the public learned they were even dating. "He only wanted something casual, but she's in a rush to settle down, have kids, and start a family since she's getting older," an anonymous source told the magazine. That same article noted Theron did not take the breakup well.