Before he was part of one of the most well-known celebrity couples to date, Ryan Reynolds was a man about town, giving his best shot at love to some of Hollywood’s biggest female stars. It’s hard to imagine him dating anyone other than his wife Blake Lively, but he was fully immersed in numerous Hollywood romances before starting his life with her.
His dating history was far from dull. He’s dated some of Hollywood’s biggest stars and party girls. He didn’t discriminate; he’s dated so many different starlets, you’d think he was a kid trying out different ice cream flavors. From costars to rockstars, Ryan Reynolds has tried them all – and it seems that a wedding ring hasn’t quite changed his womanizing ways.
He Dated Melissa Joan Hart
Even if you know him as one of the biggest stars to date, he still had to start somewhere! One of his first breakout roles was on the television show, Sabrina, the Teenage Witch, back in 1996. It was there that he met his costar, another teen in entertainment and the star of the production, Melissa Joan Hart.
The two met on set and immediately clicked. The two teens started off their relationship strong, beginning a passionate although brief relationship. He played the young witch’s boyfriend, Seth, in the Showtime movie that would later become the show. This was the first of his many Hollywood flings–I guess he started out strong!
Melissa’s Experience With Ryan Reynolds
Roughly 20 years after their relationship, Melissa Joan Hart divulged more secrets about her relationship with Reynolds back in 2013 with the release of her memoir, “Melissa Explains It All: Tales from My Abnormally Normal Life.” She elaborated on his style and persona, and what brought the two together on set.
“Nobody looked as good with wavy blond locks and a thumb ring as Ryan did,” she explained in her book. “Though I was madly in love with James, my boyfriend of six months by then, Ryan and I spent plenty of time together.” Oh wow–it seems that Melissa was a bit unfaithful herself!
Melissa Joan Hart Is Thriving Today
Today, Melissa Joan Hart is living her best life. She met her husband, musician Mark Wilkerson, at a concert for charity where he was performing with his band Course of Nature, back in 2002. Just a year later, the two joined together in holy matrimony. They’re still married to this day!
The two left Hollywood and moved back east in pursuit of a life out of the spotlight. Together, they have three happy children and couldn’t be better. They live in Westport, Connecticut with their family, living life at their own pace. Many fans are disappointed to see that she didn’t end up with one of her many on-screen boyfriends; it appears that her life turned out pretty well!
He Dated Traylor Howard
One of Ryan Reynolds’ first notable acting gigs was in a television show called Two Guys, a Girl, and a Pizza Place. This was where he met actress Traylor Howard, who was 10 years older than him. The pair met on set, and they were both main characters in the production.
It’s no surprise that this led to a steamy romance! Their relationship began while they were filming the show, and Reynolds learned a lot from his time dating an older woman. Their relationship taught him a lot about love, and even though their relationship had a clear expiration date, they lasted for almost a year.
They Kept Up Their Professional Relationship
Their show was renamed, and the relationship didn’t last, but they ultimately kept up their professional relationship. Even though things didn’t work out romantically for the pair, they managed to keep their cool while working with each other on set. The two continued to be costars until 2001.
There was a ton of speculation that their characters didn’t end up having many (if any) romantic storylines because their relationship didn’t work out. Who knows, though–not everyone has the chemistry needed to make a relationship work, fictional characters included! At least both of their characters found love at some point.
What’s Traylor Howard Getting Up to These Days?
The game of love is difficult to win; just ask Traylor Howard. She’s been married three times! Her first marriage was to actor Cameron Hall, best known for his role as Billy Shreiber in Valley of the Dolls. They were married in 1991 for just a couple of years, with their marriage ending in 1993.
Her second marriage was to actor Christian Navarro, and the two were bound together in holy union from 2003 to 2006. The two had a child together, or so it’s believed that her son Sabu is Navarro’s son. In 2011, she married Jarel Portman, and she had her second child, a son named Julien, in 2012.
He Dated Kristen Johnston Back in the Day
Ryan Reynolds is known for his smooth moves, and it appears that he’s a magnet for beautiful women. He has managed to snag some of the most prominent stars in his quest for love, including actress Kristen Johnston of 3rd Rock From the Sun fame. The two dated back in 1999.
Many fans were shocked to see the two come out together, showing off their relationship for the first time by showing up to the premiere of “Green Mile” together. They were all for showing the world that they were together, always showing up close and in hand.
Johnston Spills the Juice
While appearing on an episode of Watch What Happens Live With Andy Cohen, actress Kristen Johnston felt it was a good time to divulge some details about her relationship with Ryan Reynolds. She started to answer some of the questions that we’ve been stirring over for years.
Though she really only had good things to say about her former relationship, she shared that it had been a while and she’d forgotten. “It was so long ago I forgot, but literally, so nice, great guy, lovely,” she said. “Lovely person.” Maybe he’s not so memorable?
Kristen Johnston Is on Her Way Back Up
Even winning an Emmy doesn’t guarantee a lifetime of success! She is a Primetime Emmy Award winner, taking the cake for her role in 3rd Rock from the Sun as Sally Solomon. Things since then haven’t quite been the best for her, and fortunately she was able to reflect on it herself.
In recent interviews, Johnston has opened up about dealing with addiction in the past, using a variety of different substances. She managed to get her act together and has been clean for more than a decade! She went on to become an advocate for others who are also suffering from addiction.
His Relationship With Rachael Leigh Cook
Known for her part as the token nerdy chick in “She’s All That,” Ryan Reynolds didn’t need to take off her glasses to see her value and beauty. After Reynolds and Johnston broke up, he was linked to actress Rachael Leigh Cook. The two began dating quite quickly after his breakup.
Reynolds seems to be pretty adept at stealing hearts, especially those with other film and television stars. His relationship with the actress from Josie and the Pussycats wasn’t perfect, but it also didn’t last long, either. They dated in 2001 for a short period of time, and fans were disappointed to see it end so quickly.
They Were Both Rising to Fame
Neither Cook nor Reynolds talked too much about their relationship in the public eye. There are any number of reasons for them to break up, but it’s a great question for fans to speculate over. Why would this seemingly perfect couple break up? Why couldn’t they last longer?
It could be a pretty simple answer, really. Both Cook and Reynolds were early in their careers, and even though his has appeared to take off way more than hers has, they both had to develop more to have their careers in Hollywood take off. It appears that their relationship didn’t work out because they were both early in their careers.
How’s Rachael Leigh Cook Doing Today?
After splitting with Reynolds, something great happened for Cook. She started dating fellow actor David Gillies back in 2001 after her breakup from Reynolds. Cook and Gillies were married in 2004 and had two children together. They had a daughter in 2013 and a son in 2015.
Unfortunately, this relationship did not last a lifetime, either. The couple announced their split in mid-2019, deciding to go their separate ways after about 15 years of marriage. It appears that the actress is currently single, and maybe even looking at her next big career move.
He Messed Around With Party Girl Tara Reid
After playing the role of Van Wilder, the lead of National Lampoon’s film Van Wilder, Reynolds met Tara Reid on set. She was portrayed as his on-screen love interest and their chemistry was unmatched. Whether or not the cameras were rolling, they knew that they had something special.
Fans everywhere were shocked when they didn’t hear about a confirmed relationship between the two. Rumors are often rooted in truth, though – you might have heard through the rumor mill that they were involved romantically just off set. What do you think was the case?
Were They Just Rumors?
The rumors of a Reid and Reynolds relationship might have been just that – rumors. The two entertainers did have a chemistry that no one could deny while they were on the set of “National Lampoon.” Not only were their characters compatible, but, apparently, they were, too.
The two appeared on TRL together, which definitely did not help the rumor mill. Reid was one of the most prominent actresses in the comedy world at the time of their appearance, mostly because of her key role in the American Pie franchise.
What’s Tara Reid Up to These Days?
Tara Reid’s love life has been nothing short of active since she appeared to be involved with Ryan Reynolds. In 2010, she was reportedly engaged to Michael Axtmann, but the two decided that their relationship wasn’t meant to last forever. They called it off after only three months.
Things got a little weird with Reid after, though. She dated Michael Lillelund and claimed they got married in August 2011, but oddly enough, he denied the claim. The same month, she said that she married Zachary Kehayov before explaining it wasn’t a legal marriage. It seems that since then, she’s learned about the value of keeping her love life private.
He Was Charmed by Alyssa Milano
Ryan Reynolds was known for his roles in many romantic comedies. One of his earliest roles was in the 2002 film Buying the Cow. He was cast as a womanizer, playing opposite Alyssa Milano. If you’ve seen the film, you could understand why there was so much gossip around their relationship.
They made a cute couple on screen, but were they really involved with each other? The two claimed that nothing ever happened between them, but we know that’s not the case. It’s hard for us to confirm without them, but official relationship or not, they sure do make an attractive couple.
Was It the Right Match?
There are a few things that make us question the validity of a relationship between Reynolds and Milano. Just a couple of years before the two appeared side by side in their romantic comedy, Milano split from her ex Cinjun Tate. Not everything lasts forever!
A Reynolds and Milano relationship struck many fans as unlikely. No one anticipated that they’d do anything romantic with the other, especially because Milano was already romantically linked to one of her costars from Charmed, Brian Krause. For his part, Reynolds was about to get into one of his most serious relationships to date…
Alyssa Milano Is One of Today’s Biggest Stars
Alyssa Milano did a great job with becoming a household name! She’s done a great job on screen as well as in her personal life. She dated her Charmed costar Brian Krause for two years before they split in 2003. She realized she didn’t need him!
In 2007, Milano started seeing David Bugliari, a talent agent. They realized they were a perfect match for each other, and he proposed just a year later. They tied the knot in 2009 and had two children together. Glad you found the love that you deserve, Alyssa!
You Oughta Know (That He Dated Alanis Morissette)
Before he met the woman he’d propose to later in life, long before his days dating Scarlett Johansson and Blake Lively, he dated world renowned musician Alanis Morissette. This relationship was a doozy, for sure – it was also one of his longest relationships to date.
The two started dating back in 2002, and they were even engaged from 2004 until 2007. They had a solid five-year relationship but unfortunately never made it down the aisle as planned. They never got to say “I do,” and Reynolds even stated that he felt like they were already married.
Unhappily Ever After
The two broke up and the musician wrote a breakup anthem about him. She wrote “Torch” which appeared on her album “Flavors of Entanglement” and later admitted that it was indeed about him. The two ended their relationship quite abruptly after being engaged for years, so fans speculated about why that happened.
The singer has since blamed herself for the end of the relationship. “I get angry at myself for staying in relationships way too long,” she said. The two did not have a ton in common, and reportedly fought a lot toward the end of their days together. Hopefully things worked out for her!
Alanis Morissette Got the Love She Deserved
Back in 2010, Morissette finally got her happy ever after. She met Mario Treadway, best known as the hip-hop artist and rapper Souleye. The two were married and went on to have three children together, born in 2010, 2016, and 2019.
If Alanis and Ryan had stayed together, who knows what would have come of the relationship. Luckily, she found her perfect match, and she was able to draw some musical inspiration from the end of her relationship with Reynolds. Thanks for that, Mr. Reynolds, you’re a true inspiration!
He Dated Kristin Booth
This movie star is no stranger to romantic comedies, as made evident through his many acting credits. When he starred in the 2003 film Foolproof, his on-screen chemistry with costar Kristin Booth was undeniable. They’d engage in grand heists together in their many scenes, and they’d do it smashingly.
When the film was released, fans could sense that something was going on between the two. I mean, wasn’t it obvious that they were crazy about each other? Sources close to the stars claimed that something romantic was brewing between the two, but nothing was confirmed… at the time.
Some Unreasonable Desires
After seeing the two on screen, fans prayed that the on-screen romance was more than just that. They manifested, hoping to see a real relationship come out of their on-screen one. The fans wanted to see the actors from their favorite productions become something more than just friends. That wasn’t quite possible at the time, for a couple of reasons.
When Reynolds and Booth appeared in the film together, Reynolds was already engaged to Morissette. Even if he’s got rumors stirring about him every now and then about being unfaithful, it doesn’t appear that was the case with him and Booth. Their careers went in opposite directions, which may or may not be related.
What Is Kristin Booth Up to Today?
After Foolproof, Booth went on to act in a couple of other features. Some films included projects like At Home by Myself… With You, as well as The Calling. Booth hasn’t been the most active in the entertainment industry, so let’s just hope it was a choice she made to step out of the spotlight.
Her love life didn’t fizzle out completely after her relationship with Reynolds came to a close. She found love and married composer and musician Tim Ware back in 2008. The two joined together in holy matrimony and have clearly been avoiding the spotlight for one reason or another.
More Than Just Friends With Amy Smart
When they filmed “Just Friends” back in 2005, Ryan Reynolds and actress Amy Smart worked closely. The audience sensed an instant chemistry between the two, and they hoped that they were seeing more than just a couple of actors getting along – they wanted a real love story between them.
The film itself was very successful. It followed a young professional who has to stop home in New Jersey after a storm grounds his flight. He returns to his hometown where Smart’s character remained, and Reynolds’ character Chris Brander is determined to make her fall in love with him.
More Than Just Friends
Around the same time that the movie was released, there were some rumors stirring about something romantic happening between the two leads. Both stars denied the allegations, but we all know that there was something going on between them – something strange and steamy was afoot.
This was another relationship believed to be during his engagement to Alanis Morissette. Fans can speculate all they want, but it might not be the best use of their time. Even if they missed their window in real life, things seemed to work out OK for their characters in Just Friends.
Where Is Amy Smart These Days?
Actress Amy Smart has done pretty well for herself after Just Friends. She’s gone on to appear in several successful movies, including Avengers of Justice: Farce Wars as well as appearing in several guest roles of some pretty iconic television shows. Can you guess which?
Amy Smart had a stint on Shameless, as well as on the show Justified. She also made some appearances on Scrubs and Felicity. She got married to Carter Oosterhouse in 2011, and the two have a daughter together named Florda. Smart struggled with fertility, but fortunately was able to have a baby of her own.
He Was Serious About Scarlett Johansson
Maybe he was a serial dater, maybe he just instantly connected with some more than others. Scarlett Johansson was one of those people he connected with quite quickly. Not only did the two date seriously for some time, but they even got married in secret! They were married for two years before calling it quits.
They managed to keep their nuptials a secret from paparazzi for a moment, but they ultimately realized that they couldn’t keep their relationship going if there were always long distances between them. She was already well on her way to becoming one of the most recognizable names in Hollywood, and they couldn’t hold back. He vowed to never marry again after they split.
Things Just Weren’t Meant to Be
The two may have loved each other, but they were still seen as too competitive with each other. They clicked and clashed because they were two of a kind – and there can only be one alpha in the relationship. It was widely believed that their competitiveness led to their separation.
Both entertainers have matured and learned from their experiences over the years. Johansson stated that her age might have contributed to it all; “I mean, the first time I got married, I was 23 years old,” she shared. “I didn’t really have an understanding of marriage. Maybe I kind of romanticized it, I think, in a way.”
Scarlett Married Colin Jost
After splitting with Reynolds, the actress didn’t have a hard time finding her next love. The award-winning actress went on to date French businessman Romain Duriac, and they were together from 2014 until 2017. They had a daughter together before heading their separate ways, as well.
Shortly after her split from Duriac, she met SNL star and head writer Colin Jost. They hit it off instantly and were together for a while before tying the knot officially in a small ceremony in the summer of 2020. It looks like everything’s coming up Scarlett!
He Dated Isla Fisher
One of his more prominent relationships in the public eye was with actress Isla Fisher. This gorgeous redhead starred alongside Reynolds in the film Definitely, Maybe, about a father telling his daughter the story of how he met her mother – but which of his previous lovers would become his wife?
The two play an unlikely couple, and he proves his love for her through some over-the-top gestures – like hunting down an antique book that her deceased parent had given her. It was believed that their chemistry on screen alluded to a real relationship, but it was never confirmed.
Isla Lived Happily Ever After
Back in 2002, the Oman-born Australian actress met satirist Sacha Baron Cohen. They instantly knew that they were meant to be together and dated for two years before getting engaged in 2004. They took their time and weren’t married officially until 2010. Since then, they’ve gone on to have three beautiful kids together.
Isla remains one of the most recognizable names and faces in the entertainment industry – especially in goofy, rom-com types of movies. She’s still acting, but one of the best parts of being as successful as she became is that she doesn’t have to work if she doesn’t want to!
He Dated Sandra Bullock
Before making his way to the woman he would build his family with, Reynolds made a few pit stops along the way. As he was healing from his divorce from Scarlett Johansson, he had a brief fling with Miss Congeniality herself, award winning actress Sandra Bullock.
The two met in Texas in 2011, and rumors stirred about the two becoming involved. Their fling didn’t last too long, and they probably just realized that they weren’t going to last forever. Not long after they went their separate ways, Reynolds connected with the woman he would marry, Blake Lively.
What’s Sandra Up to These Days?
Sandra Bullock found love for herself both before and after her fling with Reynolds. She was married to American entrepreneur Jesse James from 2005 until 2010 and has been with her partner Bryan Randall since 2015. She’s one of the most recognizable faces in Hollywood – with or without a record of previous celebrity relationships.
Outside of her relationships, Sandra Bullock is always keeping busy. She’s always working on some project and was the centerpiece for many well-known projects, including The Proposal, which she starred in alongside Reynolds. She’s also recently known for her leading role in Bird Box.
He Was Hot for Charlize Theron
Reynolds was maybe the luckiest man on earth, if you look at this long list of the star’s relationships. Back in 2011, he had a fling with actress Charlize Theron. This would be the last relationship he’d have before settling down with his current wife, Blake Lively.
The two spent a long, hot summer together before ultimately choosing to head their own ways. They were destined to end up with different people, and they always knew they could depend on the other as a friend. I guess things just worked out the way that they were supposed to in this case!
What’s Charlize Theron Been Doing?
After her fling with Reynolds had met its expiration date, Theron went on to adopt two children on her own in 2012 and 20125. Right on, Charlize! She and Sean Penn started dating and were engaged in 2014, but after just six months, they decided that it was time to go in separate directions.
Since her relationship with Penn ended, Theron has stayed out of the romantic limelight. She’s constantly choosing herself, her children, and her career over her relationships and, really, who can blame her? She’s investing in herself – something we should all learn from!
The End of the Dating Game
Reynolds finally met his match when he started dating actress Blake Lively. She’s a perfect 10, or honestly, she might even be on a scale all her own. She’s best known for her role as Serena van der Woodsen on the CW’s show, Gossip Girl, which ran for years. She and Reynolds met on the set of Green Lantern.
The two started out as platonic friends, but that only allowed their relationship to grow into something strong with a stable foundation. The chemistry between them was undeniable, and after sparks started flying, they never stopped! It must be nice to find someone who is a perfect match!
He Found His Forever Lady With Blake Lively
These two have become one of the most recognizable and prominent couples in Hollywood. Just because they’re loved, doesn’t mean they’re free from controversy, though. Their wedding venue itself caused a huge stir, because many fans saw it as ignorant – they got married on a former plantation in South Carolina.
The two were married back in 2012, on a plantation that was actually the filming location for the iconic film The Notebook. One other tricky piece: The star of that film is one of Blake’s ex-boyfriends, Ryan Gosling! Funny coincidence, right? Maybe… or maybe it’s just weird?
Relationships Take Work, Take It From Ryan and Blake
These two celebrities are more in love than ever, but they’ve survived many struggles together. They’ve survived divorce rumors, they’ve survived infidelity rumors, and they’ve worked through everything that they need to, or so it seems. No relationship is perfect, and these two are continuing to work on it every day.
Now, the two have built a beautiful family together. They are crazy for each other and wanted to share their love with some children. The couple has three daughters together, and Reynolds is hopefully leaving his womanizing days behind as he becomes a family man!