Ryan Reynolds and Ryan Gosling are arguably the most handsome pairs of Canadian men ever. Hilarious, likable, and handsome as hell, both Ryans have endeared themselves beyond the borders of Canada and been beloved around the world. In fact, they have become so adored that, since making their way to stardom, both men have racked up an impressive number of exes over the years.
Both dudes may have started out in the early 1990s, but it wasn’t until later in the decade – or, in the case of Gosling, the early 2000s – that they really began to catch the hearts and eyes of women everywhere. From costars to women they met through mutual friends to setups and back to costars, these guys have worked their way through some of the most beautiful actresses in Hollywood, only to end up with two women each man can’t help but gush about.
Going from playas to devoted husbands and fathers might sound boring to some, but, to hear these guys talk about the women in their lives is to know that they are true, impossibly in love with the lives they’ve built for themselves. We know how happy Ryan Reynolds is with wife Blake Lively and how blissful Ryan Gosling is with partner Eva Mendes, but what about the women who came before them? Let’s go through the tunnel of love to take a trip down memory lane!
16 Ryan Reynolds: Melissa Joan Hart, 1996
Before the ICONIC TV show Sabrina, the Teenage Witch, we had a movie, which came out in 1996. While Sabrina on TV gave us the adorable Harvey Kinkle, Sabrina the movie gave us vintage Ryan Reynolds, bad hair and all! Fortunately for Melissa Joan Hart, though, she saw beyond the mop on his head and knew the cutie that lay beneath.
In 2013, Melissa revealed that Ryan had tried to woo her while on the set, even going so far as to purchase a pricy Beluga watch once shooting wrapped!
Clearly, the watch was the way to Melissa’s hart – at least for a while. After their one and only date, Melissa admitted in an interview with Chelsea Handler that she had a steamy makeout session with the actor, explaining, “You get a piece of jewelry like that, you gotta [kiss] the guy!” Too bad for Ryan, though, that their love affair was so brief. According to Melissa, she thought the age difference between the two of them (she was 19, he was 17) was too much for him, and told him so, ending this truly ‘90s fling as quickly as it had begun.
15 Ryan Reynolds: Traylor Howard, 1998
It seems that when Ryan was a younger man, he definitely had a thing for older ladies! Case in point: his Two Guys, a Girl, and a Pizza Place costar Traylor Howard, who was 10 years his senior at 32 in 1998, during the first season of the show.
This was before we really got to know Ryan Reynolds, and before he became the muscle-bound dude we know and love, thanks to the success he found in the 2000s.
In the 1990s, though, he was still just a small-screen stud who managed to bag Traylor, who he dated for eight months! Since the show lasted until 2001, totaling four seasons, though, we hope it wasn’t awkward around the set...
We don’t know exactly what went down between the two since it was before Ryan was very famous – and thus gives us a lack of juicy gossip – but Traylor did end up too hard up in the end. Following her split from Ryan, she ended up nabbing another bonafide hottie the following year: George Clooney! Traylor has since gone on to marry two more times (she was first married from 1991 to 1993, prior to meeting Ryan and entering into acting).
14 Ryan Reynolds: Kristen Johnston, 1999
Generally considered an odd couple, even as far as ‘90s standards go (which gave us other strange pairings, like Robert Downey Jr. and Sarah Jessica Parker, Matthew Perry and Julia Roberts, and Robert De Niro and Naomi Campbell),
Ryan Reynolds was showing that he still had a type when he briefly dated 3rd Rock From The Sun star Kristen Johnston in 1999, who was nine years older than him!
They even hit the red carpet together, as you can see here, where they’re attending the premiere of the film The Green Mile!
At six feet tall, Johnston was paired with the much-shorter Wayne Knight in the kooky sitcom, so it must have been a nice change of pace for her to have her arm around the six-foot-two Ryan! And, while Kristen may not be as famous as she once was, or topping the “Most Beautiful People” lists, she was one of the most gorgeous actresses on TV when Ryan had her! Like most of his relationships that were brief and came before he hit the big time, we don’t know a whole lot about this couple but hey, at least we have solid proof that they were once definitely an item!
13 Ryan Reynolds: Rachael Leigh Cook, 2001
With Two Guys, a Girl, and a Pizza Place winding down in 2001, Ryan was becoming a bit more famous – or at least, as famous as a Canadian actor on a small TV sitcom in the early 2000s can be! At the same time, actress Rachael Leigh Cook was riding a nice wave of popularity into the new millennium, thanks to the success of films like She’s All That (1999) and Josie and the Pussycats (2001).
However, while Ryan’s star was slowly rising, Rachael’s was on the brink of dimming, but that meant that this brief coupling managed to meet each other in the middle! At one point, Rachael had to fly to England for a film, which would have dampened their budding relationship, except Ryan showed that he had the romantic skills to pay the bills early on in his career! Instead, he pulled out of his filming schedule and went to surprise her in London, something that allowed the couple to date for around a year or so, before eventually calling it quits. Fortunately for Ryan, he had his newest film, Van Wilder, coming out and, as it turns out, it would be the first project that really allowed him to build up a resumé.
12 Ryan Reynolds: Alanis Morissette, 2002 – 2007
Ah, Alanis Morissette. Ryan’s first high profile romance was yet another one that the public didn’t really see coming. Sure, both parties were Canadian and brunette, and…well, that’s about it! Back in 2002, the pair met at a birthday party for actress Drew Barrymore, and became engaged in 2004, after two years of dating. It seemed pretty blissful for the pair of Canucks, with Alanis gushing to People,
“He’s just such a supportive creature. I feel so loved by him, in a trampoline kind of way. He’s always very happy for me.”
Alas, despite those sweet sentiments, it was not to be, and the couple called off the engagement and ended their relationship entirely in February 2007. As a form of catharsis, Alanis penned an entire album into which she poured her feelings about Ryan and their breakup, which became 2008’s Flavors of Entanglement. One song in particular, “Torch”, was about her grief over the breakup, which discusses everything she misses about Ryan. Allegedly, there might have been differing values that ultimately came between the couple, and it seemed that Ryan moved on far more quickly than his next, to his next leading lady.
11 Ryan Reynolds: Scarlett Johansson, 2007-2010
Following the very public and painful split from musician Alanis Morissette, one might think that Ryan would take some time. However, as we just mentioned, the actor didn’t need much time to heal his heart because, a mere two months later, he went public with his new romance with sultry Hollywood actress Scarlett Johansson! And this was no rebound romance either – just over a year later, in May 2008, the gorgeous pair announced their engagement. In fact, apparently, they had already been betrothed “for a little while” but had waited to announce the news!
By September 2008, the pair tied the knot in a small ceremony on Vancouver Island. Despite both parties being quite famous at the time, almost zero images of them exist – this one was taken at the 2010 Tony Awards and is allegedly the only time they were photographed at an event together! Like his relationship before, the marriage dissolved, ending in a motion for divorce in December 2010.
For her part, Scarlett obliquely referred to her divorce from Ryan as the result of “competitive” natures, stating, “[Marriage] takes a lot of work. It takes a man who’s not only confident in the love that you have for one another but confident in what he has going on in his career.”
10 Ryan Reynolds: Sandra Bullock, 2011
If you noticed the chemistry between Ryan and co-star Sandra Bullock in the 2009 film The Proposal, it might not have been just acting! According to various reports, the two were actually briefly an item in 2011 following his divorce from Scarlett Johansson. But is it true?
According to Sandra, no. While the timing would have been perfect, following her messy divorce from Jesse James a year earlier, she informed reporter Al Roker at the 2011 Golden Globes,
“I think there will be a collective sigh amongst women in the United States when I say, he’s not my lovah, he’s just an amazing friend I’ve had for 10 years. And I hope there’s more friendship like that, but I don’t get his loving after dark.”
Mutual friends of the pair also brushed aside the possibility of them being involved, despite spending New Year’s together, saying, “The danced together. They ate together. They laughed a lot. But I didn’t see any making out or anything.” Of course, tabloids being what they are, yet other insiders said the two were briefly involved, and that ex Scarlett was okay with it because the actress “likes and respects [Sandra] so much”!
9 Ryan Reynolds: Agnes Fischer, 2011
Now, this is a relationship we know for sure really happened, and, if Sandra Bullock is included as well, then Ryan had a really busy year! In 2011, he struck up a short relationship with German model Agnes Fischer. Agnes had a small, uncredited part in the film Safe House, which was filming in South Africa and which was where Ryan met the then-24-year-old blonde.
While Agnes was hardly known on our side of the world, she’s plenty famous across the pond, appearing on numerous magazine covers for publications like Runner’s World, Health & Fitness, and Shape, as well as in ads for brands like Bebe, Reebok, and Adidas. Clearly, Ryan was going back to his original type, after a brief foray into brunette territory! Since his ex-wife Scarlett Johansson was busy being wooed by the much-older Sean Penn, it almost makes sense that Ryan would look for something younger! Another relationship that was more of a fling than anything serious, the world quickly forgot about the pair once they split, and Agnes seems to have faded from the public eye. (Of course, if you’re still interested in learning about her, you can peep her Instagram account)
8 Ryan Reynolds: Charlize Theron, 2011
Another lady that Ryan Reynolds and Sean Penn have in common: Charlize Theron! In the summer of 2011, both recently out of long-term relationships (Charlize had split from actor Stuart Townsend, with whom she’d been involved for nine years), mutual friends set up this genetically-blessed pair, who had what we can only imagine being a pretty wild two months before ending their affair.
According to Us Weekly, Ryan was the one to pull the plug on their brief relationship, because “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.”
(At the time, Ryan was 35, Charlize was 36.) While the couple had once been neighbors and had known each other for years, it was their different goals and conflicting work schedules that ultimately tanked them. The same insider explains that, while Charlize didn’t expect either of them to be in it for the long haul, she “didn’t take it very well when he broke it off” and was “pretty bummed about it all.”
Well, it seemed that Ryan wasn’t tied to the idea of keeping things casual after all, so long as the right woman came around.
7 Ryan Reynolds: Blake Lively, 2011 – Present
Finally, we reach the end of Ryan Reynold’s dating history, as he wooed, bedded, and wedded some of Hollywood’s most gorgeous and talented actresses before finally settling down with current wife Blake Lively, with whom he shares two daughters, James and Ines.
Meeting on the set of the superhero box office bomb The Green Lantern in 2010, sparks didn’t fly until a year later, when they were on a double date with other people. Sound awkward? According to Ryan, it was – for their dates! “That was the most awkward date [from their perspective] probably because we were just like fireworks coming across.”
The beautiful twosome tied the knot in a small ceremony in 2012 on a plantation in South Carolina and welcomed their first child in 2014, and their second in 2016. Adorable one and off the red carpet, with complementary senses of humor, a killer social media game that has them regularly teasing one another, a devotion to their family, an understanding that family comes before career, and shared pride in one another’s work, it seems that in Blake, Ryan has truly met his perfect match – it just took him nine tries to get there!
6 Ryan Gosling: Sandra Bullock, 2002 – 2003
Just the first instance in which both Canadian Ryans share lady loves, we have Sandra Bullock and Ryan Gosling! (Although, to be fair, Ryan Reynolds never ‘fessed up to dating Sandra, unlike this Ryan, who was regularly seen canoodling with the A-list actress.) After meeting on the set of their 2002 film Murder By Numbers, Ryan and Sandra began seeing each other and actually lasted for a year together, despite the 16-year age gap. (Ryan was 22 at the time, while Sandra was 38.) Seen together at multiple events, out and about, and on the red carpet during their short courtship, these two weren’t afraid of the PDA, even if Sandra was painted as a “cougar” for dating Ryan.
Even though the couple didn’t last – and both moved on to much more high-profile romance – there’s still fond memories and friendly love between the two. In a 2011 interview with the UK-based newspaper The Times, Ryan stated, “I had two of the best girlfriends of all time. I haven’t met anybody who could top them.” Sandra was obviously the first girlfriend he was talking about, while the second was the next entry on our list!
5 Ryan Gosling: Rachel McAdams, 2004 – 2007
Of course, the next and arguably most recognizable relationship Ryan Gosling has ever been in was with his costar in the romance film The Notebook, fellow Canadian Rachel McAdams!
While they met on-set in 2042, it wasn't exactly 'love at first sight'. According to director Nick Cassavetes, the pair couldn’t stand each other during filming! At one point, Cassavetes dished that Ryan demanded another actress come stand in for Rachel, telling him, “I can’t. I can’t do it with her. I’m just not getting anything from this.” Other times, the pair reportedly screamed at each other in a room before eventually working out their differences.
Despite all that drama, the couple finally got together a year later, in 2005. However, like their fiery characters and the messy relationship they endured, Ryan and Rachel went through not one, but two breakups. The first one, apparently, was mutual, with Ryan informing GQ magazine, “The only thing I remember is we both went down swingin’ and we called it a draw.” (In this same article, he referred to Rachel as “one of the great loves of my life”.)
In 2008, the pair decided to rekindle their romance, but it only lasted a few months, as on-again, off-again relationships tend to do, with the couple citing “busy schedules” as the reason for their second – and final – split.
4 Ryan Gosling: Kat Dennings, 2009
After splitting from Rachel McAdams, Ryan decided to take things easy for a while and embarked on a few short relationships for the next couple of years. First at-bat: 2 Broke Girls actress Kat Dennings.
The rumors that these two were seeing each other began when someone spotted them at Disneyland together in 2009 and proceeded to tweet about running into the couple. At the same time, Kat’s own Twitter account was updated to mention that someone special had taken her away for a day at the theme park, allowing users of the social media to connect the dots and realize that this pair were now seeing each other!
However, it’s never been a rumor that’s been proven to be true, by Ryan or by Kat. In an MTV interview the same year, when someone asked if she was out at Disneyland with “a friend”, Kat sharply responded, “A friend? I don’t have any friends,” before finishing with, “I don’t know. I can’t talk about my personal life.” Ryan had remained similarly tight-lipped, and perhaps it’s for the best. With only one Disneyland date between them (that we know of), there must not be much of a story to tell!
3 RYAN GOSLING: Blake Lively, 2010
How’s this for borrowing girlfriends? Shortly before Blake Lively got married to her own Canadian – Ryan Reynolds – she saw the OTHER Canadian Ryan! Despite filming a Chanel ad in Paris the day before in December 2010, Blake quickly jetted to New York City to watch the VIP premiere of Ryan’s film Blue Valentine. Except, they did more than just watch a movie! According to witnesses, the couple was making out most of the night during the after party! While they left separately, there was much touching and whispering between the two. Prior to that over the top mack session, Ryan and Blake had been spotted grabbing ice cream together in October at – you guessed it! – Disneyland!
According to a friend who was close to Ryan (at least at the time), “They’ve been out a few times and are definitely into each other, but I don’t think it’s super serious or anything right now. Yeah, they’re casually dating, but I could see it becoming more.” At the time, Blake had split from her Gossip Girl costar Penn Badgley, and Ryan was having fun playing the field with a few Hollywood starlets, but it was just a short time before they both settled down – with other people, that is.
2 RYAN GOSLING: Olivia Wilde, 2011
Another relationship that was never confirmed, but was as good as official, thanks to eagle-eyed fans, we have Ryan Gosling and Olivia Wilde, who may or may not have been involved for a brief period in 2011.
Olivia had filed for divorce from her first husband, Tao Ruspoli, whom she married after six months together, and Ryan was still casually seeing a bevy of beautiful actresses, Wilde included. While in Cincinnati filming The Ides of March, a fan spotted Ryan and Olivia out on an aquarium date, despite the fact that they had done the Hollywood disguises of baseball caps and sunglasses, and caught the whole thing on tape! (You can actually watch it all for yourself).
Before the aquarium date, both beautiful people were seen at a Golden Globes after party, allegedly flirting up a storm! One insider said, “When Olivia saw [Ryan] at the after party, she went right up to his table. They were talking and laughing together for a long time. They looked cute!” Neither star nor their reps confirmed or denied the relationship, but it doesn’t matter all that much, because it’s the next woman on this list who stole Ryan’s heart for good.
1 RYAN GOSLING: Eva Mendes, 2011 – Present
Like Ryan Reynolds and Blake Lively, Ryan Gosling and Eva Mendes also met while filming a movie: 2011’s The Place Beyond the Pines. Like a few of the lovely ladies already mentioned on this list, the Mickey Mouse Club alum also took Eva to Disneyland on a date, where they were seen holding hands, sharing food, and hugging between trips on rides.
By 2014, the couple had welcomed their first of two daughters, Esmeralda, with the second coming along in 2016, named Amada. Unlike Ryan and Blake, Ryan and Eva have been markedly more private when it comes to their personal lives, both as a couple and as a family. Almost no images exist of the pair’s children and in fact, Eva has taken a bit of a break from acting in order to raise their kids. Clearly, their relationship is built on mutual respect, love, and admiration, with Ryan telling Hello! Magazine that the one thing he looks for in a woman is “that she’s Eva Mendes. There’s nothing else I’m looking for.” In the same interview, he proclaimed about the mother of his daughters, “I know that I’m with the person I’m supposed to be with.” Awww!
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