Reynolds had a pretty colorful dating history before he and the “Gossip Girl” actress settled down. From costars to singers, here are the women Ryan Reynolds was romantically linked to.
Melissa Joan Hart - 1996
Before Ryan Reynolds was one of Hollywood's hottest actors, he was making his way into the industry. One of his breakout performances was his part in the television production of "Sabrina, the Teenage Witch," back in 1996. He and Melissa Joan Hart met while on set, and the two teens began a passionate yet short-lived fling.
It makes sense; after all, they were only teenagers at the time. Nevertheless, their relationship left a mark on them both, and it's safe to say that this relationship would be the first of many for the young actor.
Melissa Explains It All
Nearly 20 years later, more truths surfaced regarding Melissa Joan Hart's and Ryan's brief relationship. In 2013, the actress elaborated on the romance in her memoir, " Melissa Explains It All: Tales from My Abnormally Normal Life."
"Nobody looked as good with wavy blond locks and a thumb ring as Ryan did,” she explained. “Though I was madly in love with James, my boyfriend of six months by then, Ryan and I spent plenty of time together.”
Melissa Joan Hart - Today
Melissa Joan Hart met her husband, Mark Wilkerson, at a concert for charity where he performed with his band, "Course of Nature" in 2002. A year later, the couple tied the knot and are still married today. Leaving Hollywood was a big yet essential step for the actress, as she has three kids with the musician.
Melissa and her family live in Westport, Connecticut, and though some fans are sad that Sabrina and Seth didn't end up together, it looks like her life took a successful turn.
Traylor Howard - 1998
The Canadian actor's first significant gig was a TV show called "Two Guys, A Girl, and a Pizza Place" back in 2000. He met Traylor Howard on set. The actress, who was ten years his senior, and Ryan starred as the title characters and sparked up a romance while filming the show.
Having a relationship with an older woman taught Reynolds a lot about love, and though it was destined to fail, the couple lasted for almost a year, breaking up after eight months.
Keeping Things Professional
Though things didn't work out romantically between Ryan and Traylor, the two actors managed to keep a professional relationship while working on the show that was renamed, and we know today as "Two Guys and a Girl." The exes remained co-stars until 2001.
There have been speculations that the failure of their real-life relationship might have influenced the lack of romantic storylines between the two characters. Of course, their names end up with other people by the end of the show.
Traylor Howard - Today
Traylor has had a tumultuous love life; she has been married three times. Her first marriage was to actor Cameron Hall in 1991, which ended in 1993. Her second was to actor Christian Navarro, from 2003 to 2006.
In 2006 she gave birth to a son, Sabu. In 2011, she found love for the third time and married Jarel Portman; the two have a son, Julien, born in 2012.
Kristen Johnston - 1999
Ryan Reynolds is a TV star chick magnet. After his breakup from Traylor Howard, the actor started dating Kristen Johnston, a "3rd Rock From the Sun" actress, back in 1999.
The two actors were an unlikely couple, so it was surprising to fans everywhere when the duo showed up at the premiere of the "Green Mile" together.
A Lovely Person
While the details surrounding their short relationship have been unclear for years, Kristen Johnston recently revealed some more juice about her time spent with the heartthrob actor. During an episode of "Watch What Happens Live," Johnston began opening up a little.
She only had good things to say about what it was like dating Reynolds. She told Andy Cohen, “It was so long ago I forgot, but literally, so nice, great guy, lovely,” she declared. “Lovely person.”
Kristen Johnston - Today
Though she is a Primetime Emmy Award-winning actress for her role as Sally Solomon in "3rd Rock from the Sun," Kristen hasn't had an easy life. In recent interviews, Kristen admitted that she had a past addiction to various substances, but now she has been clean for more than a decade.
She has also become an advocate for people that suffer from addiction. She encourages them to speak out and seek help. Other than that, she keeps her private life private, so we don't know what's happening to her romantically!
Rachael Leigh Cook - 2001
Rachael Leigh Cook portrayed the nerdy girl in "She’s All That" until Freddie Prinze Jr. took her glasses off. After Ryan Reynolds and Kristen Johnston broke up, the actor was romantically linked to Rachael Leigh Cook in 2001.
When it comes to sparking up relationships with film and television stars, Ryan Reynolds is the guy. Unfortunately, his relationship with Rachael didn't last as long as fans were hoping it would.
At the end of the day, both Rachael and Ryan have been quiet about the details surrounding their short-lived romance back in the early 2000s. Perhaps the reason the two actors didn't last was their budding careers.
Though Ryan's career has lifted off much more than Rachael's, they were both on their way to stardom at the time. Reynolds had just landed a role as Van Wilder in 2002, and Cook starred in the film "Josie and the Pussycats."
Rachael Leigh Cook - Today
Something good came out of Rachael and Ryan's breakup, that's for sure! The actress started dating fellow actor David Gillies after she and Ryan split in 2001. The two married in 2004 and had two children together, a daughter, born in 2013, and a son born in 2015.
Sadly, the couple announced they were splitting in mid-2019. They had decided to go their separate ways after nearly 15 years of marriage. It seems like the actress is currently single; perhaps she focuses her energy on a major comeback in her career?
Tara Reid - 2002
In 2002, Ryan played Van Wilder, the lead role in the movie "National Lampoon’s Van Wilder." Tara Reid portrayed his love interest, and their chemistry both and offset was excellent.
Everyone was surprised when they didn't become a couple, especially since they were both single at the time. Though, we have heard through the grapevine that they had a short affair behind the scenes. What do you think?
Rumors Spread but Were Never Confirmed
While the rumors of their relationship were never confirmed, the chemistry between the two actors on the set of "National Lampoon" was undeniable. The fact that their characters were so compatible in the movie definitely made many curious about the nature of their relationship.
Their shared appearance on "TRL" also fueled rumors at the time. Tara Reid was one of the most prominent comedy stars at the time, thanks to her role in the "American Pie" series.
Tara Reid - Today
Tara has had quite an eventful love life. In 2010, the actress got engaged to Michael Axtmann, but the two decided to go their separate ways just 3 months later. She then dated Michael Lillelund, declaring she married him in August 2011. Oddly, he has denied this claim.
That same month, she said she married Zachary Kehayov but later explained that it was not a legal marriage. From 2013 to 2014, she dated musician Erez Eisen. Reid has learned a thing or two about keeping her love life private and has since seemed to have kept this part of her life off the public radar.
Alyssa Milano - 2002
Ryan was a big rom-com actor in the early 2000s. In the 2002 film "Buying the Cow," he was cast as the stereotypical womanizer opposite the "Charmed" star, Alyssa Milano. If you've watched the film, it's easy to see that these two connect, which is probably why gossip arose on set.
Though they made a cute movie couple, the actors claimed that nothing ever happened between them. Though we'll never know for sure, it's nice to imagine what could have been if the two had been official.
The Questionable Duo
Though it's hard to admit, there are a couple of reasons why a romance between Milano and Reynolds may have been unlikely. A couple of years before starring in their rom-com, Milano had split from Cinjun Tate.
It seemed unlikely that she would have begun anything romantic with Ryan, seeing as she was romantically linked to her "Charmed" co-star Brian Krause at the time. Reynolds was in the midst of beginning one of his biggest romances yet...
Alyssa Milano - Today
After "Charmed," Alyssa Milano became very successful both on-screen and off. Aforementioned, she dated her "Charmed" co-star Brian Krause for two years; the couple split in 2003.
In 2007, she entered a romantic relationship with David Bugliari, who proposed a year later. The beautiful couple tied the knot in 2009 and welcomed two children.
Alanis Morissette - 2002-2007
Before there was Scarlett Johansson or Blake Lively, there was Alanis Morissette. The couple was engaged from 2004 to 2007, they had a solid five-year relationship, but they never walked down the aisle. Though they never said their "I do's," Ryan has stated that he felt as though they were married.
After the breakup, the famous musician wrote a song about Reynolds in which she mourned over their former connection. The song “Torch” appeared in her album, Flavors of Entanglement. She has since admitted that she wrote the song for Ryan.
Not so Happily Ever After
Over the years, fans have wondered why Alanis Morissette and Ryan Reynolds broke up so suddenly after being engaged years. Since the breakup, Morissette has admitted that she blames herself for the relationship's demise.
“I get angry at myself for staying in relationships way too long,” she's explained. She also revealed that she felt like the two didn't have much in common, and they fought a lot towards the end of their relationship.
Alanis Morissette - Today
In 2010, Alanis Morissette finally walked down the aisle when she married Mario Treadway, aka Souleye, the hip-hop artist and rapper. They have three children together, born in 2010, 2016, and 2019.
It’s safe to say that her life took a turn for the best after she and Reynolds parted ways. The relationship she had with Reynolds and the consequent breakup was an inspiration for her music, so at least there's that!
Kristin Booth - 2003
Reynolds forte seems to be romantic comedies; that's why it came as no surprise when he starred in the 2003 film "Foolproof." He had amazing on-screen chemistry with Kristin Booth. In the film, the two carry out grand heists together, and they were great together.
After the film's release, fans hoped their chemistry would shift into reality. Some sources claimed that the duo's friendship was developing into something "more," though nothing was confirmed.
Not So Foolproof
Following the premiere of "Foolproof," fans shipped a great love between Booth and Reynolds. For those unfamiliar, "shipping" is the desire by fans for either real-life or fictional characters to be in a relationship. Their desire was unreasonable, considering Reynolds was in the midst of his engagement to Alanis Morissette.
Interestingly enough, Reynold and Booth's careers have gone in two completely different directions. Which brings us to our next question, where is Kristin these days?
Kristin Booth - Today
After Foolproof, Kristin went on to act in several films, including "At Home By Myself…with You" and "The Calling," which was her last big-screen flick.
When it comes to her love life (which, let's be honest, is all anyone really cares about anyway), Kristin has mostly kept quiet. In 2006, she married composer and musician Tim Ware.
Amy Smart - 2005
While filming "Just Friends" in 2005, Ryan worked closely with Amy Smart. Their chemistry on-screen was so believable; they caused viewers to fall in love.
The film was a huge success and told the story of Chris Brander, who, after being disconnected from his childhood best friend for many years, comes back to his hometown, determined to make her fall in love with him. Of course, the actors' chemistry on-screen was so strong; people wondered if something was happening between the two behind the camera.
So, Were They Just Friends?
When a movie with the name "Just Friends" comes out, rumors about the two lead actors being more than just friends will circulate. Both denied allegations, so we'll have to come to terms with never actually knowing what went on between the two.
Though, at the end of the day, it seems unlikely considering he was still in a relationship with the Canadian musician Alanis Morissette. So what has Amy Smart been doing since then, where has life taken her?
Amy Smart - Today
Amy has gone on to act in many successful movies, including "Avengers of Justice: Farce Wars" and "The Single Moms Club." She's also made her way to the silver screen starring in episodes of shows like "Shameless" and "Justified."
Smart has been smart about her love life, unlike most Hollywood stars, keeping it out of the limelight. So, we're unsure of her current relationship status!
Scarlett Johansson - 2007-2010
Ryan Reynolds bounced from one serious relationship to another; this time, he found love with Scarlett Johansson. This time around, Ryan did end up tying the knot, but kept their marriage very discreet, away from paparazzi and red carpets. They were married for two years before splitting.
Presumably, the main reason for their separation was the fact that they had to sustain their relationship over a long distance for much of the time, and Johansson wasn't a big fan of this. After his marriage ended with Scarlet, Ryan vowed never to marry again.
Too Young and Competitive
Another surprising reason they split was their competitiveness; they were both of the same. One of the other factors that led to Scarlett Johansson’s separation from Ryan Reynolds was their rumored competitive streak. Moreover, it is believed that they fought a lot.
Scarlett has matured plenty since her marriage to Reynolds and has admitted that her young age played in part in their ultimate divorce. “I mean, the first time I got married, I was 23 years old,” she explained. “I didn’t really have an understanding of marriage. Maybe I kind of romanticized it, I think, in a way.”
Scarlett Johansson - Today
After she and Reynolds went their separate ways, the award-winning actress started seeing French businessman Romain Duriac. They were together from 2014 to 2017 and had a kid together before splitting up. Their daughter, named Rose Dorothy Dauriac, was born in 2014 in New York City.
In 2017 she met SNL star Colin Jost, and the two hit it off. In 2020 the couple married, and by the look of things, it seems like Scarlett has finally found the one!
Isla Fisher - 2008
Perhaps one of his more memorable roles, Reynolds starred in the film "Definitely, Maybe" alongside Isla Fisher. Yet another romantic comedy starring the Candian heartthrob, we were laughing and cooing as the two fell in love. Of course, it wasn’t that hard to see the unusual chemistry these two bestowed on-screen.
While nothing has ever been said about the two sparking up a romance behind the scenes, we can't help but daydream about what a cute couple these two might have made.
Isla Fisher - Today
In 2002, Isla crossed paths with Sacha Baron Cohen, and the rest was history. The couple dated for two years before getting engaged in 2004, and in 2010 they got married. The beautiful couple has three children together and is one of Hollywood's strongest couples.
Isla still acts and has recently been in "Arrested Development" and films such as "Keeping Up with the Joneses." Baron-Cohen is most well-known for his role as "Borat."
Sandra Bullock - 2011
After healing from his divorce from ScarJo, he had a few flings before he met the mother of his children. One of these was a short romance between him and the award-winning actress, Sandra Bullock.
Rumors flew that the two talented actors were flirty and coy when they met in Texas in 2011. Though we would have loved to see their romance blossom, it was presumed to be a short-lived fling. Shortly after, Reynolds connected with Blake Lively.
Sandra Bullock - Today
Sandra Bullock was married to American entrepreneur Jesse James from 2005 until 2010.
In their five year courtship, the couple had two kids together, both adopted. In 2010, Bullock filed for divorce, citing a “conflict of personalities.”
Agnes Fischer - 2011
It seems like 2011 was a good year for Ryan Reynolds. According to "People," Reynolds was spotted with the German model Agnes Fischer a couple of months after his divorce. As we know, things don't stay quiet for long in Hollywood, and rumors that the two were dating were in almost every tabloid magazine.
Some reports say that they only dated for a month, though as far as Hollywood goes, a month is practically a lifetime! The model wasn't on anyone's radar until she was caught hanging with Reynolds, which was an excellent career move (if you can call it that) for her!
Agnes Fischer - Today
Besides Reynolds, the German model was also romantically linked to the Thirty Seconds to Mars handmade, Shannon Leto.
According to multiple sources on the internet and her own social media accounts, Fischer is not currently romantically linked to anyone!
Charlize Theron - 2011
As we've seen in this long list of beautiful ladies, Ryan Reynolds loved surrounding himself with talented and gorgeous women. In 2011, he had a fling with Charlize Theron, the last woman in Ryan's life, before he settled down with Blake Lively.
After spending the sweet summer together, Charlize and Ryan decided to go their separate ways, subsequently understand they had different priorities.
Charlize Theron - Today
After her fleeting relationship with Ryan ended, Theron adopted two children in 2012 and 2015. She entered a relationship with Sean Penn, and the two got engaged in 2014. Six short months later, they called off their engagement.
Since Penn, Theron has not been spotted with any new love interests, and it seems like she is choosing herself, her children, and her career over men. In the years since her breakup from Ryan, her career has flourished, and we can't wait to see what the world has in store for her.
Blake Lively - 2011-Present
Blake Lively is most notorious for her role as Serena van der Woodsen on the CW drama, "Gossip Girl." She and Ryan met in 2011 when they were filming "Green Lantern." At first, they decided to keep their relationship completely platonic, but the chemistry between them was so strong that sparks began to fly.
It seems like the two were meant to be together, and in 2012, they married. They have since welcomed three daughters together and are one of the most loved couples in Hollywood.
Though they are loved by all in Hollywood, they aren't exempt from controversy. Their wedding venue was one of these matters. The couple married on a former plantation in South Carolina.
The plantation also served as the set for everyone's favorite love story, "The Notebook." It may seem romantic, but it's filled with irony when you think about the fact that Lively used to date the lead of the film, Ryan Gosling.
Morena Baccarin - 2016
If you thought the story ended here, think again! Considering he's been with so many cast-mates, this one didn't come as much of a surprise.
At one point, rumors circulated that Reynolds had had an affair with his co-star from "Deadpool," Morena Baccarin. The rumors were constantly denied, and neither he nor Lively let the gossip get in the way of their marriage.
Morena Baccarin - Today
In 2015, Morena declared that she would marry her "Gotham" costar, Ben McKenzie. She was pregnant with their daughter, and six months later, she was born!
The couple announced that they were engaged late in 2016 and were married on June 2, 2017 - which also happens to be Morena’s birthday.
Monica Ruiz - 2019
In 2019, Monica worked on a Peloton ad called “The Gift That Gives Back." It generated tons of controversy after its release. Monica plays the spouse who gets a lot of controversy after its release on television. In the ad, Monica Ruiz plays a spouse who gets a stationary bike as a Christmas gift from her husband.
After the backlash passed, Reynolds hired Ruiz for his Gin aviation commercial. Of course, this sparked rumors that something was going on between the two. They both denied the claims, and Reynolds's kindness helped Ruiz relaunch her career.
Monica Ruiz - Today
Monica married Christopher O’Malley in 2013. They have a daughter and a son together. When she was pregnant with both of her kids, Monica did a lot of maternity modeling.
She has kept her private life out of the limelight, especially since the controversy she sparked in the Peloton commercial.
Headed to Splitsville?
Part of being a celebrity is knowing that fans will relentlessly come up with rumors about you. Of course, Hollywood's favorite couple would be the victim of all of these rumors!
The reports about Reynolds’ impending divorce have been countless. One of the rumors even suggested that Lively had gotten back together with her ex, Leonardo DiCaprio.
Far From the Truth
Luckily this was far from being true; the duo is more powerful than ever. They are so strong, in fact, that they don't have a problem poking fun at the rumors and speculations of them breaking up. It seems like Ryan and Blake will have an ongoing battle with Hollywood, proving to everyone how happy they are together, despite rumors and gossip.
Perhaps fans should just be content with the fact that the couple lives a wonderful life together, with their three daughters?
In the eight years that they've been married, Ryan Reynolds and Blake Lively welcomed three daughters: James, Betty, and Inez. However, Reynolds opened up that over the fact that he never thought he'd be raising all girls.
You see, Reynolds comes from an all-boy household. He has three older brothers; being the youngest of four boys made it hard for him to imagine he would have three girls of his own.
Of course, he loves being a girl, dad. He even has a couple of secrets to parenting success, keeping it simple yet effective: being there for his girls. “I just try to be as present as possible. We don’t split up like I shoot movies, and my wife shoots movies, and we go travel all over the place, and we just all go together," Reynolds revealed.
"I think that’s been the best part of it is that we really don’t spend a lot of time apart. I get to spend a lot of time with my girls.”
The True Superheroes
Ryan Reynolds is sure that the women in his life are "superheroes" like they are in his movie. He explained that they are the most capable people he knows and that if anyone were to go wrong, the women in his life are the first people he would lean on.
According to the actor, they have wisdom, strength and are calm under fire. Though Reynolds doesn't open up about his daughters often, there's no doubt he's loving being his girls' dad.