Younger millennials and Gen Z kids might find it hard to believe that there was life before Ryan Reynolds became a husband to Blake Lively and a father to their three daughters. Once upon a time in Hollywood, Reynolds was a sought-after bachelor, and his dating history was wild and varied.
Ryan Reynolds dated actresses, singers, and even his co-stars. Below are a few of the famous women who were able to call Reynolds their “bae” before Blake Lively ever did. Hint: You might be surprised by a few of them. Others will have you digging up old shows you used to love as a kid. Enjoy!
Sabrina’s Melissa Joan Hart (1996)
Before Ryan Reynolds was on Hollywood’s A-list, he was part of a beloved television production during the 1990s. As a teenager, Reynolds was a member of the cast of Sabrina, the Teenage Witch. It was in 1996 when he and the star of the show, Melissa Joan Hart, met and started a short-lived relationship.
They were teenagers, after all, and their youthful relationship made an impression on them both. Essentially, this relationship was the first of many for the young Reynolds.
Melissa Tells The Truth
After two decades, the truth surfaced about the brief relationship Melissa Joan Hart and Ryan Reynolds had. In the actress’s 2013 memoir, Melissa Explains It All: Takes from My Abnormally Normal Life, she finally spilled the tea.
Hart described Reynolds as someone who looked good despite his thumb ring and wavy blond hair. At that time, Hart was in a relationship with her then six-month boyfriend, James. However, she and Ryan spent most of their time together.
Where is Melissa Joan Hart Now?
Melissa Joan Hart is now married to her husband, Mark Wilkerson. The two met in 2002 at a charity concert where Wilkerson performed with his band, Course of Nature. After a year, they got married, and they are still living happily ever after. Hart left Hollywood to take care of her three children with the musician.
Melissa currently lives with her family in Westport, Connecticut. Though Sabrina fans are sad that Reynolds and Hart didn’t end up together, there’s every reason in the world to wish them well because they are both living happily ever after with their respective partners.
Traylor Howard – The Girl in the Pizza Place (1998)
Reynolds was also on a television show called Two Guys, a Girl, and a Pizza Place. It was on the set of this show where the actor met actress Traylor Howard. Though the actress was ten years Ryan’s senior, the two hit it off during the show.
Being in a relationship with a much older partner allowed Reynolds to learn a lot about love. Unfortunately, their relationship didn’t last. The two broke up after a mere eight months.
The Show Must Go on
Though Ryan and Traylor’s courtship didn’t work out, the two were able to maintain their professional relationship. Their show was renamed Two Guys and a Girl, and it lasted until 2001.
Speculations were rife that the lack of a romantic storyline between the two was due to the failure of their real-life relationship. Whatever the case, they were able to perform on-screen together without a problem. They both went on to enjoy relationships with other people before the show came to an end.
Where Is Traylor Howard Now?
Since then, Traylor’s love life has been tumultuous. The actress has been married three times. The first was in 1991 with actor Cameron Hall. Their relationship ended in 1993. She got married again a decade later to actor Christian Navarro. The marriage lasted until 2006.
She gave birth to a baby boy in 2006, but the relationship with Navarro didn’t last. Traylor finally found the love of her life in 2011 and got married to Jarel Portman. She gave birth to their son, Julien, a year later.
Third Rock From The Sun Star Kristen Johnston (1999)
By now, Ryan Reynolds was a relatively famous TV star and a certified chick magnet. After his relationship with Traylor Howard, he began dating Kristen Johnston of Third Rock From The Sun fame. The two were together in 1999.
The pair was seen as such an unlikely couple that fans of the show were surprised when they saw the two attend the premiere of The Green Mile. We told you some of the entries on this list would surprise you! Who wants to go watch reruns of Third Rock From The Sun now?
Reynolds Is a Lovely Person
The two didn’t reveal much about their time together, and a lot of things were not clear after their relationship ended. Fortunately, Johnston revealed some juicy details about Reynolds in an episode of Watch What Happens Live.
Fortunately for Reynolds, she only had good things to say. According to Johnston, “It was so long ago I forgot, but literally, so nice, great guy… a lovely person.” How sweet! It’s nice to hear someone speaking kindly about an ex.
Where Is Kristen Johnston Now?
Despite being an Emmy Award-winning actress thanks to her Sally Solomon character in Third Rock from the Sun, Kristen Johnston's life is not a bed of roses. She’s admitted to having an addiction to illicit substances. However, she has declared herself clean and sober for ten years now.
She is also an advocate for people suffering from addiction. Kristen actively encourages everyone to speak out and to ask for help. However, she is also a private person, so very little is known about her romantic life.
Rachael Leigh Cook of She’s All That (2001)
Rachael Leigh Cook was the nerdy girl in She’s All That. But when Freddie Prinze Jr. took away her glasses, she “miraculously” became a gorgeous woman. No wonder Ryan Reynolds was linked to her romantically in 2001 after he broke up with Kristen Johnston.
Ryan Reynolds was, by this time, an expert at creating relationships with up-and-coming film and TV stars. Ryan and Rachel certainly made an adorable couple. However, as we all know, their relationship didn’t last.
Rising Young Stars
In the early 2000s, Rachael and Ryan were silent about their brief romance. The reason why their relationship didn’t last may have been due to their burgeoning careers. However, we’ll never truly know what went on as it was all so long ago.
Back then, the two had opportunities to reach full-fledged stardom. Ryan's career was flourishing as he bagged the role of Van Wilder back in 2002. Meanwhile, Rachael was starting in the teen movie Josie and the Pussycats.
Where Is Rachael Leigh Cook Now?
Despite their breakup, something good came out of their relationship. The actress began dating co-actor David Gillies after her breakup with Reynolds in 2001. They got married three years later. Their union produced two children, a daughter in 2013 and a son in 2015.
Unfortunately, they announced their split in 2019. The couple parted ways after being married for 15 years. Rachael is currently single and is focusing on making a Hollywood comeback. She recently joined the cast of He’s All That – a remake of her 2001 film.
Van Wilder Co-star Tara Reid (2002)
It was in 2002 when Ryan Reynolds played the character Van Wilder in the movie National Lampoon’s Van Wilder. He had the lead role while actress Tara Reid (who starred with Rachel Leigh Cook in Josie and the Pussycats) was his love interest. Their chemistry translated on-screen and was equally obvious off-screen.
Alas, their relationship did not last, despite the fact that everyone was rooting for the couple. According to the grapevine, they only had a short affair while working on the movie.
Unconfirmed Rumors
The two never confirmed the rumors about their relationship, despite their romantic behavior on the set of Van Wilder. Their on-screen compatibility could not be denied, so a lot of people were curious about the real nature of their relationship.
When the two appeared on TRL, the rumors were further fueled. Tara Reid’s popularity as a comedy star due to her appearance in the movie American Pie almost made her America’s darling. Sadly, she went downhill after Van Wilder.
Where Is Tara Reid Now?
Tara’s love life has been eventful. She was engaged to Michael Axtmann in 2010, but they decided to separate after three months. She eventually got married in August 2011, and everyone assumed it was to Michael Lillelund. However, Michael was shocked by the claims, revealing that Tara had actually married Zack Kahayov.
In the same month, Tara Reid also clarified that she got married to Kahayov. However, she explained that the union was not legal. Reid also dated Erez Eisen, a musician, from 2013 to 2014. Currently, Reid prefers to keep her love life private, so very little is known about her personal life.
Alyssa Milano of Buying the Cow (2002)
Ryan Reynolds became a sought-after romantic comedy actor in the early 2000s. He appeared in the movie Buying the Cow in 2002, playing a womanizer. He co-starred with Charmed actress Alyssa Milano. The two connected on-screen, and their chemistry was palpable. Tongues wagged about what went on behind the scenes of the movie.
They were a very cute couple in the film, so it was only natural that everyone wondered if they ever became an item. However, both claimed that nothing went on between them romantically. It would have been nice to see them both together for real and not just “for reel.”
Are They or Aren’t They?
There are actually valid reasons why Milano and Reynolds probably didn’t entertain a relationship. At that time, Milano had just broken up with Cinjun Tate. It wasn’t the ideal time for her to be starting a relationship with anyone new. However, a fling may have been just what she wanted.
Milano was also romantically linked to Brian Krause, her Charmed co-star. Meanwhile, Reynolds was also in the middle of starting his most popular romance yet. So, all in all, we tend to believe them when they say that nothing really happened.
Where Is Alyssa Milano Now?
When Charmed ended, Alyssa Milano continued to have success on-screen and off-screen. She eventually dated Brian Krause, her Charmed could-star, until the couple split in 2003.
She then started a relationship with David Bugliari in 2007. David proposed after a year. The two got married in 2009 and now have two kids. Milano recently appeared in the controversial Netflix series Insatiable. Though the show only ran for two seasons, there’s no denying that Milano is currently living a “Charmed” life after all.
Singer Alanis Morissette (2002-2007)
Isn’t it ironic that Alanis Morissette was in a relationship with Ryan Reynolds? They even got engaged! The couple was actually in a relationship for five solid years. However, they did not walk down the aisle. According to Reynolds, they did not need to as they already felt as if they were married.
When Reynolds and Morissette did break up, the singer wrote the song “Torch” as an expression of grief for the end of their relationship. The song was included in the album Flavors of Entanglement. It was only after the album’s release that she admitted that the song was for Reynolds.
Alanis Blamed Herself
A lot of fans were curious as to why the two broke up after years of being together. Morissette has since acknowledged that she blames herself for the relationship’s end.
Alanis explained that she stayed too long in relationships despite having little in common with her partner. According to the singer, “I get angry at myself for staying in relationships way too long.” As their breakup loomed, she revealed that they had been fighting a lot and knew it was not going to work out.
Where Is Alanis Morissette Now?
Alanis Morissette finally found the love of her life and walked down the aisle with Mario Treadway, a hip-hop artist also known as Souleye. Since their wedding, they have had three children. Alanis looks very different since becoming a mother. Notably, her signature long hair has been cut super short.
Morissette has been living her best life after parting ways with Reynolds. She used the relationship and her breakup with the actor as inspiration to create more music. Everything turned out for the best!
Kristin Booth of Foolproof (2003)
Reynolds seemed to be stuck on romantic comedies during the 2000s. In 2003 he starred in Foolproof with Kristin Booth. Similar to the story with his previous co-stars, Reynolds and Booth had palpable on-screen chemistry. The movie was about love and pulling off heists – all the fun stuff!
However, neither of them stole the other’s hearts because their on-screen relationship did not translate into reality. Though sources did claim that their friendship was evolving into something “more.” We wonder what that means.
Not a Foolproof Relationship
During the premiere of the movie Foolproof, fans tried their best to pair the two together by “shipping” them. The term is used to refer to fans who want fictional characters to end up together in real life. However, their desire was not possible as Reynolds was engaged to Alanis Morissette at the time.
Since then, Booth’s and Reynolds’ careers have headed in different directions. Are you wondering what Kristin is doing now? Don’t worry – we’ve got you covered!
Where Is Kristin Booth Now?
Since the movie Foolproof, Kristin continued to act in various films such as At Home By Myself…with You. Her last movie was The Calling. According to her Twitter profile, she is now a Pilates instructor and a “professional pretender.”
Her personal life remains personal, though. She prefers to keep quiet about her relationship. She did marry musician Tim Ware in 2006, and Booth describes herself as a “mom” and “wife” on Twitter. It sounds like she’s perfectly happy with the life she’s built for herself since Foolproof.
Just Friends with Amy Smart (2005)
While shooting the 2005 movie Just Friends, Ryan Reynolds and Amy Smart were able to work closely together. Again, Reynolds had considerable chemistry with his co-star. They were so convincing that viewers fell in love with their pairing.
The movie was also a box office success. Reynolds played the character of Chris Brander – a man estranged from his childhood best friend. When Brander goes back to his hometown, he is determined to make her fall in love with him. The movie left a lot of fans wondering if there really was a relationship brewing between the co-stars.
Were They in a Relationship?
It was easy to link these Just Friends stars together because their movie was all about them being “just friends.” However, the two have consistently denied they were ever in a relationship, so fans had to keep guessing whether they were ever romantically involved.
It seems highly unlikely they were ever together as Reynolds was in a relationship with singer Alanis Morissette back then. Fans of the movie are wondering, what is Amy Smart doing now? We have the answers coming right up.
Where Is Amy Smart Now?
Since Just Friends, Amy proceeded to star in a lot of successful movies, such as Avengers of Justice: Farce Wars and The Single Moms Club. She's also appeared in many episodes of shows such as Shameless and Justified.
Fortunately, Smart was wise when making life decisions and getting into relationships. She is now living the “happily ever after” life with her husband, Carter Oosterhouse. The two have been married since 2011, and they had a daughter via surrogate in 2016.
Scarlett Johansson (2007-2010)
Ryan Reynolds had been bouncing from one relationship to the next until he found what he, and everyone else, thought was the love of his life. He met actress Scarlett Johansson, and the two tied the knot discreetly far from the red carpets and paparazzi. Unfortunately, their love didn’t last, and they split after two years.
One of the reasons for the separation was their long-distance relationship which Johansson disliked. Reynolds seemed to have sworn off marriage after his breakup with Johansson. Indeed, he publicly declared that he didn’t want to get married ever again.
They Were Both Competitive
According to Scarlett, one reason for the breakup of their marriage was their mutual competitiveness. Both had careers that were flourishing, and the pressure to be successful seemed to weigh on both of them. It is also believed they fought a lot during the relationship.
In later interviews, Scarlett showed her maturity as she looked back at her marriage with Reynolds. She admitted that being young played a part in their divorce. According to Johansson, “I mean, the first time I got married, I was 23 years old. I didn’t really have an understanding of marriage. Maybe I kind of romanticized it, I think, in a way.”
Where Is Scarlett Johansson Now?
When Reynolds and Johansson divorced, the actress began dating French businessman Romain Dauriac. Their relationship lasted from 2014 to 2017. The two had a child prior to breaking up. Their daughter was born in New York City in 2014.
Three years later, Johansson finally met the person she describes as the love of her life, Colin Jost. The SNL star and Johansson hit it off, and the pair got married in 2020. Scarlett clearly has a thing for funny guys!
Isla Fisher of Definitely, Maybe (2008)
One of Reynolds’ most popular roles was in the rom-com movie, Definitely, Maybe. His co-star this time was Australian actress Isla Fisher. The Canadian heartthrob made fans coo because of his chemistry with Fisher.
They were such a cute couple on screen that many hoped they would also become a real-life couple off-screen. Imagine how adorable they would have been. We can see why fans were shipping them so hard. The question is, did anything come of it? Let’s find out!
Where Is Isla Fisher Now?
When Isla Fisher met actor Sacha Baron Cohen in 2002, the two seemed to be destined to be together. They dated for two years prior to their 2004 engagement. Eventually, they got married in 2010. The couple now has three children together, and they are famous for having one of the strongest marriages in Hollywood.
Isla can still be seen acting in shows such as Arrested Development and in the movie Keeping Up with the Joneses. Meanwhile, her husband Baron-Cohen is best known for his Borat character.
Sandra Bullock (2011)
Reynolds and Sandra Bullock’s 2009 movie, The Proposal, had everyone entertained. After Ryan’s divorce from Scarlett, he had a few short relationships, one of which was with his co-star, Sandra.
Rumors abound that the two A-listers were acting coy and flirty with each other when they were seen together in Texas back in 2011. Though fans of The Proposal would have loved to see a real relationship blossom, it seems the two only had a short-lived fling. At this time, Reynolds was already in communication with Blake Lively.
Where Is Sandra Bullock Now?
Sandra Bullock was married to the heavily tattooed American entrepreneur Jesse James from the years 2005 to 2010. So, when she filmed The Proposal, she was barely on the other side of their rather controversial split.
Their courtship lasted five years. The pair adopted two children. However, Bullock filed for divorce in 2010 and cited a “conflict of personalities” as the reason for the split. Of course, the tabloids were quick to spill the news of Jesse’s repeated infidelity.
German Model Agnes Fischer (2011)
2011 seemed to have been a good year for Ryan Reynolds. Among other things, he was spotted by People magazine with Agnes Fischer, a German model. The two were seen together a few months after Reynolds’ divorce. Instantly, rumors spread that the pair were dating. But were the stories true?
Reports revealed that the two dated only for a month – a lifetime by Hollywood standards. Also, Fischer suddenly became popular after being seen with the Hollywood actor. So, some people wondered if the model dated Reynolds as a career move.
Where Is Agnes Fischer Now?
Fischer was also linked to Jared Leto, the quirky actor and Thirty Seconds to Mars frontman. However, very little is known about their relationship. Indeed, of all the famous women on this list, we suspect Fischer is probably the only one you haven’t heard of before.
This is because Fischer likes to keep a low profile. Various sources have revealed that she is currently not in a relationship with anyone. However, it’s hard to say as she’s just not the type to find her way into the tabloid press.
Charlize Theron (2011)
Ryan Reynolds clearly has a penchant for dating talented and gorgeous women. Another one for the list is actress Charlize Theron. She was said to be the last woman he dated prior to getting hitched to Blake Lively.
Theron and Reynolds reportedly spent the summer together until they decided they had to go their separate ways. The two agreed their priorities were different, so a long-term relationship just wouldn’t make sense. We’re big fans of people making mature decisions about their relationships.
Where Is Charlize Theron Now?
After Theron’s relationship with Ryan ended, the actress decided to adopt children in 2012 and 2015. She was also in a relationship with Sean Penn. Their relationship was so serious they even got engaged in 2014. However, they broke off the engagement after six months.
Theron seems to have chosen herself, her children, and her career above men. Since she broke up with Reynolds, her career continued to flourish. Who knows what the future holds for Charlize? The only thing we’re certain of is that she’ll continue to light up our screens with her performances.
Blake Lively Is the One (2011 to Present)
Blake Lively became popular because of her role as Serena van der Woodsen on the CW drama series Gossip Girl. In 2011, Lively and Reynolds met during the shoot of the movie Green Lantern. The two initially decided to be nothing more than friends. However, their chemistry was so strong that sparks eventually started to fly.
Reynolds and Lively seemed destined to be with each other. They got married in 2012 and now have three daughters. They are currently one of Hollywood’s most beloved couples.
Happily Ever After
Though they are a power couple, they are still not immune to controversy. This was proven when they decided to hold their wedding at a former plantation in the South. People were not impressed with this venue as it held a dark history connected to slavery.
However, the same plantation was also seen in the romantic movie, The Notebook. While this sounds romantic, it actually added an extra layer of awkwardness to the situation as Blake once dated the star of The Notebook, Ryan Gosling.