Melissa Joan Hart - 1996
Like many actors, Ryan Reynolds had to take many small, supporting roles before he made it big in the industry. One of these was as Seth in the 1996 television movie Sabrina, the Teenage Witch. Melissa Joan Hart played the titular character, and Reynolds played her love interest. Like their characters, the two young actors had a teenage romance, though it didn’t turn into a long-term relationship.
They were both carefree, fresh-faced, and embarking on similar journeys to build their acting careers. It makes sense that they explored their romantic connection at the time of filming.
Looking Back Fondly
It was a brief relationship, though Melissa looks back fondly on it. In 2013, she mentioned their romance in her memoir, Melissa Explains It All: Tales From My Abnormally Normal Life, and also revealed that she had a boyfriend named James at the time. While her boyfriend was “cute and charming”, she also “spent plenty of time” with Ryan, and, ultimately, didn’t end up with either of them. In 2017, she also called Ryan “a really nice guy”.
Ryan hasn’t spoken publicly about Melissa, but it’s clear that they were happy spending time together in their youth and then went their separate ways, which is natural for young people who are still discovering themselves.
Melissa Joan Hart - 2025
Melissa Joan Hart has had a successful acting career herself over the years. She played Sabrina for seven years in the television series after the movie with Reynolds, winning several awards for her performance, including “Leading Young Actress”. She settled down in 2003 when she married musician Mark Wilkerson, and the two went on to have three children together. Though she still acts, Melissa has also found success in other business ventures, including her own fashion line.
Like Seth and Sabrina, Ryan and Melissa weren’t destined to be together forever, but things worked out well for both parties in the end. Melissa seems completely content with her happy family life.
Traylor Howard - 1998
Reynolds experienced one of his first big breakthroughs in 1998 when he played one of the lead characters in a new television sitcom titled Two Guys, a Girl and a Pizza Place. During filming, one co-star in particular caught his eye: Traylor Howard. Although Howard was ten years older than Reynolds, that didn’t hinder their romance. They kept things very private, with neither publicly disclosing details about what went on.
The relationship lasted for roughly eight months, though they continued working together until 2001, when the show was canceled due to low ratings. Things seemed amicable and filming always ran smoothly.
Remaining Good Friends
It was definitely beneficial to the show that Ryan and Traylor were able to remain friends and work well together. A sitcom requires its cast to have good chemistry, and though their characters didn’t share any romantic storylines, they still worked well alongside each other. Some people speculated that perhaps the showrunners had decided not to have Ryan’s character Michael and Traylor’s character Sharon start a relationship due to their off-screen breakup, but this was never confirmed.
In 2022, Ryan shared his hopes for a reunion, mentioning that he was still on good terms with the rest of the cast and had spoken to Traylor and another co-star the day before.
Traylor Howard - 2025
Traylor Howard continued to take roles in the years after Two Guys, a Girl and a Pizza Place, but later withdrew from acting to spend more time with her children. She has two sons, Sabu, born in 2011, and Julien, born in 2021. Before settling down with her current husband Jarel Portman in 2011, she was married twice, first to actor Cameron B. Hall in 1991 and then to Christian Navarro in 2003.
Her short relationship with Ryan Reynolds is now very much in the past, though it’s good to hear that the two are still on good terms. Fans of their sitcom are doubtless eager for a cast reunion.
Kristen Johnston - 1999
After his breakup with Traylor Howard, Reynolds dived into a romance with another recognizable television actress: Kristen Johnston. Though they weren’t co-stars, they ran in some of the same circles, so it makes sense that they developed a connection. They made their public debut at the premiere of Tom Hanks’ hit movie The Green Mile, smiling for photographers as they walked the red carpet together. They were an unexpected but welcome new couple.
In 1999, Ryan was still rising to fame in his lead role on Two Guys, a Girl and a Pizza Place, but Kristen was also riding a career high that would help her to launch a very successful career.
Brief But Lovely
Kristen Johnston was starring in the sitcom 3rd Rock from the Sun in 1999, and had already won two Primetime Emmy Awards for Outstanding Supporting Actress in a Comedy Series. Naturally, everybody was keen to know who she was dating, but Kristen kept her brief relationship with Ryan private at the time. In 2020, she opened up a bit, saying that the romance was “so long ago”, but Ryan was a “lovely person”.
Ryan has been similarly coy about their past relationship, though it’s clear there’s no bad blood between the pair. They may even run into each other at premieres or events nowadays.
Kristen Johnston - 2025
Becoming an Emmy-winning actress so early into her career definitely set Kristen Johnston up for success, though things haven’t always been easy for her. In her memoir, she shared details about drug and alcohol addictions that began when she was young and continued to plague her for years. Fortunately, she has been sober for 14 years and now uses her experience to advocate for others in the same position. She is also still acting.
Unlike Ryan, Kristen is not married, and she has mainly kept her relationships out of the spotlight. She continues to do great work while also putting her acting talents to good use.
Rachael Leigh Cook - 2001
After splitting up with Kristen Johnston, Ryan Reynolds wasn’t publicly linked to a woman until he was spotted with actress Rachael Leigh Cook. She was one of the biggest teen stars of the ‘90s and early 2000s, thanks to her roles in She’s All That (1999) and Josie and the Pussycats (2001). Unfortunately for fans of the couple, they only dated for a year before breaking up. At the time, Ryan was wrapping up his sitcom and moving on to new opportunities.
Though they slipped under the radar, things between Ryan and Rachael seemed promising. The actor even flew to England when he was supposed to be working to surprise his girlfriend on set.
Busy Lives
The reason for Ryan and Rachael’s breakup has never been publicized, but it’s likely that the two were simply too busy to commit to a long-term relationship. At the time, both were rising stars with plenty of career options open to them, and they likely would have regretted not taking the jobs they did. Rachael had five movie credits in 2001 alone, and she continued to work steadily in film and television throughout the early 2000s.
Ryan’s most major movie roles would come later in his career, but he was also striving for success back in 2001. He has kept the details of his relationship and breakup with Rachael private.
Rachael Leigh Cook - 2025
Nobody can say that Rachael Leigh Cook has not had a successful career! Though some of her biggest roles remain those nostalgic rom-com characters from the ‘90s and ‘00s, she has turned her hand to a variety of genres and picked up a few awards along the way. A few years after splitting up with Ryan, Rachael met actor Daniel Gillies, whom she married in 2004 after a whirlwind romance and short engagement.
The couple has two children, a daughter and a son. They are no longer married, but the separation seemed amicable, and Rachael is currently believed to be single.
Tara Reid - 2002
After his relationships with Johnston and Cook, Reynolds reignited his trend of being linked to his co-stars. In 2002, he played the titular character in National Lampoon’s Van Wilder, striking up excellent chemistry with his love interest, actress Tara Reid. Clearly, this chemistry translated well off-screen, too, because the two were rumored to be in a relationship. However, neither of them ever publicly confirmed this, despite eager fans hoping that it was true.
Throughout filming and the movie’s release, Ryan was continuously linked to Tara. They were both young and beautiful, and they obviously had good chemistry, so why weren’t they an official couple?
Rumor Has It
Ryan had kept all of his prior relationships private, so it would make sense that he didn’t address the rumor mill, even when people claimed that the two did have a fling. If anything did happen, both parties have remained coy about it ever since, so it likely wasn’t ever a serious relationship. National Lampoon’s Van Wilder didn’t receive the best reviews, though critics praised the chemistry between Reynolds and Reid.
At the time, Reid was a well-known name, thanks to her role as Vicky Lathum in 1999’s American Pie. People wanted to know more about her, including who she may or may not be dating.
Tara Reid - 2025
Though her presumed relationship with Ryan Reynolds was never confirmed, Tara Reid has had a much more public love life since then. Before being linked to Ryan, she was engaged to television host Carson Daly, though they broke off their engagement in 2001. In 2010, her entrepreneur boyfriend Michael Axtmann proposed at an LA restaurant, though they also called things off before getting married. In 2011, Reid announced that she was married, though the man in question, businessman Michael Lillelund, denied this claim.
Though she’s had a few more public relationships since then, Tara’s love life is currently far more private, with her various movie and television projects doubtless taking precedence in her life.
Alyssa Milano - 2002
Ryan Reynolds is known primarily for comedy now, but those roots go back far further than Deadpool. In 2002, he starred in a screwball comedy called Buying the Cow, in which he played a womanizer called Mike. Alyssa Milano, a former child star who was also working her way up in comedy roles, played Amy, and gossip soon sprung up about a potential romance between the two actors. It was never confirmed, but their on-screen chemistry seemed like a strong hint.
Buying the Cow was originally supposed to be released in 2000, but ended up being pushed back to 2002, so if anything did happen, it could have been at any point during that time frame.
An Unlikely Pair
It’s normal for fans of popular actors to imagine them sharing romantic connections, but there’s fairly little evidence to suggest that Ryan Reynolds and Alyssa Milano even had a fling. At the time, both were single, with Ryan’s last confirmed girlfriend being Rachael Leigh Cook and Alyssa having divorced singer Cinjun Tate in 1999 after less than a year of marriage. It would make sense that neither were looking for anything serious.
Neither Reynolds nor Milano has spoken up about the rumors that they were once an item, so if anything did happen, it’s being kept between them and is firmly in the past now.
Alyssa Milano - 2025
Most people probably know Alyssa Milano best for her work as Phoebe Halliwell in Charmed, but she’s continued to work steadily since then. She’s had a range of movie roles, as well as parts in successful shows like Grey’s Anatomy and Family Guy. Many also recognize her activism efforts, particularly for the MeToo movement in Hollywood. But she’s also had time for romance, marrying CAA agent David Bugliari in 2008 and welcoming two children.
As for the rumors about a Reynolds-Milano romance, it seems we’ll never know, but it’s fun for fans of the movie to imagine what their relationship could have been like off-screen.
Alanis Morisette - 2002 to 2007
After seemingly baseless rumors linking him to Tara Reid and Alyssa Milano, Ryan jumped feet-first into his first long-term relationship with singer Alanis Morissette. Though he has only been married twice, Ryan came very close to making Alanis his first wife, and the two were together for a total of five years, eventually breaking up in 2007. Ryan’s career was growing and Alanis was one of the most popular female musicians of the ‘90s. They seemed like a great match.
Ryan was obviously very serious about Alanis, even before they were engaged. The two were spotted at various red carpet events, cozying up to each other and looking very happy.
A Shock Split
After so many brief relationships and suggested romances, it seemed that Ryan had made his perfect match with Alanis. That’s why their abrupt split was so shocking. In 2005, Alanis had told reporters that they were enjoying their engagement, and Ryan said he felt like they were already married. When they parted ways, an official statement declared that they would “remain close friends”. Looking back on that time, Alanis has admitted her heartbreak and said she “grieved” the relationship.
It inspired her 2008 album Flavors of Entanglement, including the song “Torch,” which was written specifically for Ryan and includes the lyrics “I never dreamed I would have to lay down my torch for you.”
Alanis Morisette - 2025
Despite her heartbreak, Alanis did get her happily ever after a few years later. In 2009, she met rapper Mario “Souleye” Treadway at a meditation gathering in LA and married him in a private ceremony a year later. The couple has three children and still lives in LA. Since the successful release of Flavors of Entanglement in 2008, Alanis has released three more studio albums and continued touring regularly. She has also appeared in several movies.
Though things ultimately weren’t meant to be between Ryan and Alanis, both went on to find their happy endings, and likely grew as people as a result of their relationship and breakup.
Kristin Booth - 2003
Despite entering a serious relationship with Alanis Morissette in 2002, fans of Ryan Reynolds continued to read romance into his interactions with co-stars. In 2003, he starred alongside first-time Canadian actress Kristin Booth in the heist movie Foolproof. It was a fun flick about a group of friends who design plans for heists and then end up carrying one out, and the chemistry between Reynolds and Booth carried much of it.
At the time, Kristin Booth was a new actress, but Ryan had begun to make a name for himself, so people were starting to analyze all of his relationships, even the platonic ones.
Wishful Thinking
This was simply a case of “shipping”, which is when fans of two people wish for them to be in a romantic relationship. However, despite their good on-screen chemistry, there was nothing to suggest that Reynolds and Booth were anything more than co-workers. Ryan was also frequently spotted with his then-girlfriend Alanis Morissette, holding hands and kissing, so there was no basis for imagining that he’d strike up a romance with another woman.
At the time, nothing was known about Kristin’s relationship status, but she wasn’t spotted out with Ryan, so it’s safe to assume that they were simply two actors doing a job together.
Kristin Booth - 2025
After the release of Foolproof in 2003, Kristin went on to work in plenty of movies and television shows. One of her breakthrough performances came in 2007, when she portrayed a prostitute in This Beautiful City. She also played one of the main characters in the Hallmark series Signed, Sealed, Delivered and its 13 made-for-TV spin offs. As for romance, she married Tim Ware in 2006, and the two are still going strong in 2025.
Kristin seems to be quite a private person, so not a lot is known about her personal life. However, she has had a successful career, and her role in Foolproof alongside Ryan Reynolds was clearly just the start.
Amy Smart - 2005
By 2005, Ryan Reynolds was engaged to Alanis Morissette and seemed to be smitten with her. However, that didn’t stop the rumor mill from insinuating that there may have been a connection between him and another co-star: Amy Smart. The two starred as former friends Chris and Jamie, with Ryan’s character desperately trying to get out of the friendzone and start a relationship with the girl of his dreams. Some people speculated that Ryan wanted to pursue Amy in a similar fashion off-screen.
However, this was most likely another case of wishful thinking, with fans reading too much into a rom-com. Ryan and Amy had good chemistry, so people wanted them to be a couple.
Just Friends, Nothing More
Like the title of the movie, Ryan and Amy had always said they were just friends and nothing more. They were also both in relationships at the time: Ryan with Alanis, and Amy with actor and director Branden Williams. People almost always speculate about actors’ personal lives, especially when two co-stars seem like they’d work well together as a couple. If anything more ever happened between Ryan and Amy, there’s no proof of it.
The two actually reunited in 2023 to shoot a commercial for Ryan’s company Aviation Gin. It was a Christmas-themed ad inspired by Just Friends, so they both clearly look back fondly on the movie.
Amy Smart - 2025
Amy slowly grew her acting career since her first movie role in 1997, leading to big parts in the teen drama Varsity Blues, the comedy Rat Race, and the sci-fi drama The Butterfly Effect. In 2020, she even entered the DC Universe in the series Stargirl. She also married television personality Carter Oosterhouse in 2011, and the two share a daughter, who was born via surrogate in 2016.
Apart from that, Amy has also maintained her privacy, so not a lot is known about her personal life. However, it seems unlikely that there was ever anything more than friendship between her and Ryan Reynolds.
Scarlett Johansson - 2007 to 2010
After ending his engagement with Alanis Morissette in 2007, Ryan Reynolds swiftly began another serious relationship, this time with actress Scarlett Johansson. She’d found success as a child actor, then made the transition to adult roles by the time she met Ryan. Many people knew her from movies like Lost in Translation, Match Point, and The Prestige. They married after only a year of dating in a remote retreat on Vancouver Island.
They made a beautiful couple, though there weren’t actually many photos of them snapped out in public together, indicating that they wanted to keep their marriage private at the time.
Young and Successful
Though Ryan was slowly but surely growing his career when they met, Scarlett was doubtless the bigger name, with excellent movie credits and a BAFTA for Best Actress. She was also eight years his junior, but just as passionate about advancing her career. They both had busy work schedules, which is believed to be one of the reasons they ultimately separated in 2010. Scarlett also once mentioned that being in a relationship with another successful individual can lead to competitiveness.
When they split in 2010, their divorce announcement said that they’d both left the relationship with “love and kindness” and asked for privacy. Of course, people have speculated ever since.
Scarlett Johansson - 2025
Ryan Reynolds was the first of Scarlett Johansson’s three husbands. The second was French businessman Romain Dauriac, whom she married in 2014 and also welcomed a daughter with. After divorcing in 2017, Scarlett began dating Saturday Night Live writer Colin Jost. They married in 2020 and Scarlett gave birth to their son a year later. She’s also had a very successful career, famously playing Black Widow in the MCU and being nominated for two Oscars in 2020.
Many fans have even forgotten that she used to be married to Ryan Reynolds. At only 23, Scarlett married young, but she seems to have made a perfect match with Colin Jost. Third time’s the charm!
Isla Fisher - 2008
Ryan Reynolds made a big name for himself as a charming rom-com actor, which, naturally, had people more curious than ever about his own romantic life. Though he was engaged and later married to Scarlett Johansson in 2008, that didn’t stop people from noticing his chemistry with yet more of his co-stars. One of these was Isla Fisher, alongside whom Ryan starred in the 2008 movie Definitely, Maybe. Isla played a love interest of Ryan’s protagonist.
Of course, they needed good chemistry to pull that storyline off, and both actors delivered. They never dated, but many people imagined that they’d be a well-matched and attractive couple.
Isla Fisher - 2025
Isla may not have had a romantic relationship with Ryan Reynolds, but she went on to marry one of Hollywood’s most recognizable comedy actors: Sacha Baron Cohen. They met at a party in Sydney in 2002, got engaged in 2004, and married in 2010. They had three children together, but ended up divorcing in 2024. Isla has also had a great career, with movie credits including Wedding Crashers, The Great Gatsby, and Now You See Me. She has also appeared in the popular sitcom Arrested Development.
While there may have been no relationship between Ryan Reynolds and Isla Fisher, it’s fun to think about how different things could have been if they’d become an official couple back then.
Sandra Bullock - 2011
Sandra Bullock is a name that everybody knows, but not many know that she was once romantically linked to Ryan Reynolds. Fresh from his divorce from Scarlett Johansson, Ryan was linked to several women, including Sandra. They had previously co-starred in The Proposal as a businesswoman who enlists her personal assistant to pretend to be her fiance, eventually falling in love with him. Critics widely praised Ryan and Sandra’s on-screen chemistry.
It’s believed that the two had a short relationship, though they’ve never publicly addressed their romance. It’s not hard to believe that such a great connection existed behind the scenes, too.
Sandra Bullock - 2025
The Proposal was just one of a whole host of excellent performances that Sandra Bullock has given. She has been in some very successful movies, including Miss Congeniality, Ocean’s 8, Gravity, and Bird Box. In 2010, she won the Academy Award for Best Actress for her role in The Blind Side. Unfortunately, Sandra divorced her husband Jesse James that same year after multiple rumors of infidelity on his part. They had been married for five years. Sandra went on to adopt two children.
They’d have been an interesting couple, but Ryan and Sandra were ultimately not meant to be. If they had been, then maybe Ryan wouldn’t have connected with Blake Lively later that same year.
Agnes Fischer - 2011
Another of Ryan’s rumored flings after finalizing his divorce from Scarlett Johansson was with German model Agnes Fischer. The two were spotted getting cozy in Cape Town, South Africa, where Ryan was filming the movie Safe House, which came out in 2012. As soon as they were spotted spending time together, tabloids were quick to call Agnes his girlfriend, though the two never officially stepped out as a couple, no doubt to protect their privacy.
For the most part, they flew under the radar, leading many to believe that it was just a fling and may have only lasted for a month. After that, there weren’t many photos of them together.
Charlize Theron - 2011
Charlize Theron is one of the most beautiful actresses in Hollywood, so it’s completely understandable that Ryan Reynolds fell for her in 2011. The two were reportedly set up on a date by mutual friends, got along well, and began a relationship. Unfortunately, they only lasted a few months before splitting up. Some sources reported that it was because Ryan wanted “something casual”, whereas Charlize wanted to “have kids and start a family”, although this has not been verified.
It’s more likely that their busy schedules got in the way because Ryan went on to settle down with Blake Lively not long after, and there doesn’t seem to be any bad blood between the pair.
Charlize Theron - 2025
Whether the rumors about her breakup with Ryan were true or not, Charlize went on to build a family of her own. She adopted two children, one in 2012 and another in 2015. In 2013, she began a relationship with actor Sean Penn and was reportedly engaged to him, though Charlize emphasized that those rumors were false. They split up in 2015. Since then, she has had no highly-publicized partners, choosing to focus on her work and children.
Charlize Theron remains one of Hollywood’s top actors, with one Oscar under her belt and a variety of successful movies, including The Devil’s Advocate, Monster, Atomic Blonde, and Bombshell.
Blake Lively - 2011 to Present
Nowadays, everybody knows Ryan Reynolds as half of one of Hollywood’s best-known couples. They first met in 2010 while filming Green Lantern but didn’t develop a romantic connection until 2011. Ryan has said that they later went on a double date… with other people! However, he and Blake couldn’t deny their chemistry and began dating each other instead. They quickly fell in love and married one year later in Mount Pleasant, South Carolina.
Though Green Lantern may have bombed (something that Reynolds himself has joked about), one good thing came out of it. Ever since that first meeting in 2010, Ryan and Blake seemed destined for one another.
Blake Lively - 2025
In 2025, Ryan and Blake are still very much going strong. They have four children together, three daughters and a son, and reside in New York. They became one of pop culture’s best-loved couples for their witty social media banter, as well as their various red carpet appearances. However, the couple has also been met with some criticism, namely, having their 2012 wedding on a former plantation, for which Ryan later apologized.
After the release of Deadpool in 2016, Ryan leaped to new heights of fame. Blake has also maintained a respectable acting career, as well as pursuing other business ventures and raising a family in Hollywood.