All The Women In Ryan Reynolds’ Life Before Blake Lively

The two actors met on set when they were filming the movie Sabrina, the Teenage Witch back in 1996, and they had a super passionate fling that ended up being short-lived. After all, they were only teenagers at the time. Nonetheless, their short fling did leave a mark on them both. It might be safe to say that this was Ryan Reynolds’s first relationship with a fellow actress?

It would take a few years before more secrets surfaced surrounding the nature of Melissa Joan Hart’s relationship with Ryan Reynolds. In her 2013 memoir, Melissa Explains It All: Tales from My Abnormally Normal Life, the actress elaborated on her brief romance with Reynolds. “Nobody looked as good with wavy blond locks and a thumb ring as Ryan did,” she wrote. “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 met her current husband, Mark Wilkerson, at a concert for charity where he performed in a band named Course of Nature in Kentucky back in 2002. The two tied the knot in 2003, and they are still married today. They have three kids together, and the whole family lives in Westport, Connecticut. It seems that her life took a successful turn when she met her husband and started a family.

Ryan Reynolds’ first major gig was a TV show called Two Guys, A Girl, and a Pizza Place back in 2000. It was on that set where he met Traylor Howard. His relationship with Traylor, who was ten years older than him, came to an end after eight months. Having a relationship with an older woman might be tough, even for an experienced guy like Reynolds. Regardless, the couple lasted for almost a year.

Despite things not working out between Ryan Reynolds and Traylor Howard, they still managed to keep things relatively professional while working together on Two Guys and a Girl. They remained co-stars until 2001. However, many have speculated that the lack of romantic storylines between the two of them might have been influenced by the breakdown of their real-life relationship. Of course, their characters end up with other people by the end of the series. But was that the end of their romance?

Traylor Howard is a divorcée, and she might be currently single. She was married to Jarel Portman, whom she married in 2011. Till the present day, she has been married three times and has two children from previous marriages. Traylor gave birth to her daughter in 2006, and her son in 2012. She was also rumored to have dated George Clooney at one point, but we won’t get into that here.

Ryan Reynolds knew how to attract the TV stars in his life. After the break-up with Traylor Howard, he reportedly started dating Kristen Johnston, the actress from 3rd Rock From the Sun, back in 1999. Traylor gave birth to her daughter in 2006, and her son in 2012. She was also rumored to have dated George Clooney at one point, but we won’t get into that here.

While the details surrounding their brief relationship have been cloudy for years, Kristen Johnston recently revealed some more about her time with Ryan Reynolds. She started to open up a little about it during an episode of Watch What Happens Live. In short, she only had good things to say to Andy Cohen about what it was like to date the Deadpool star. “It was so long ago I forgot, but literally, so nice, great guy, lovely,” she said. “Lovely person.”

In recent interviews, the actress confessed that she had a past addiction to alcohol and painkillers – but now she has been sober for more than a decade. She also encourages people who are suffering from addiction to bravely speak out and seek help. The actress dated David Newson in 1996 and Ryan Reynolds in 1999. She has never been married. We wish her all the best and hope she will keep up the good work in supporting people who suffer from addiction.

Rachael Leigh Cook was the nerdy girl in She’s All That until Freddie Prinze Jr. took off her glasses. Apparently, after Ryan Reynolds broke up with Kristen Johnston, he had a brief fling with Rachael Leigh Cook in 2001. Ryan Reynolds is the man when it comes to snagging film and television stars; he never rests. Sadly, his relationship with Rachael didn’t last as long as everyone hoped it would.

Truth be told, both Rachael Leigh Cook and Ryan Reynolds have been coy about the details surrounding their short-lived relationship back in the early 2000s. What we do know is that the two hit it off just before Reynolds had his breakout role in 2002’s Van Wilder. Cook was also hot property in Hollywood at the time, not only for her role in She’s All That. She also starred in the movie Josie and the Pussycats.

Rachael Leigh Cook married actor David Gillies back in 2004. They started dating right after she broke up with Ryan Reynolds back in 2001. They have two children together, a daughter who was born in September 2013, and a son who was born in April 2015. Sadly, the couple announced the end of their marriage in June 2019. The couple respectfully decided to go their separate ways. Currently, the actress is single, and there is no sign of a man in her life.

In 2002, Ryan played the lead role in the movie National Lampoon’s Van Wilder. Opposite him was Tara Reid, who played his love interest – and their chemistry was excellent. We were all quite surprised that these two never officially became a couple, even though they were both single at the time. Rumor has it that they had a short affair behind the scenes. We find this quite easy to believe, especially when we consider how Ryan seems to have a thing for blonde co-stars.

While the rumors of their off-screen relationship were unconfirmed, the chemistry between Tara Reid and Ryan Reynolds on the set of Van Wilder was unquestionable. The fact that their characters hit it off in the movie definitely fueled those rumors at the time. Their shared appearance on TRL also made many curious about the nature of their relationship. Of course, Tara Reid was a sought-after comedy star around the same time as Reynolds due to her role in the American Pie film series.

Since then, Tara has had quite an active love life. In 2010, Tara got engaged to Michael Axtmann, but the two called it off just 3 months later. She then started dating Michael Lillelund late in 2010, and claimed that she married him in August 2011. Strangely, he has denied this. Later in August 2011, Tara said she married Zachary Kehayov, but later said it was not a legal marriage. In 2013, she began dating musician Erez Eisen. They stayed together for around a year. We are not aware of any relationships she’s had since then, as Tara seems to have kept her romantic life off the public radar.

The early 2000’s saw Ryan acting in plenty of rom-coms. One of these was Buying the Cow in 2002. He was cast as a stereotypical womanizer opposite Alyssa Milano, of Charmed fame. In the film, the two connect – and the fireworks were easy to see. This set the gossiping tongues wagging. While they made a cute couple in the movie, they claimed that nothing ever went further than the movie set. We guess we will never know – but it would have been interesting to see what would have happened if they had started officially dating.

There are a couple of reasons why any relationship between Alyssa Milano and Ryan Reynolds around 2002 would have been unlikely. Just a couple of years prior to starring in Buying the Cow, Milano had separated from Cinjun Tate. However, it seemed unlikely that she would have started anything with Reynolds seeing that she was dating Charmed co-star Brian Krause at the time. Moreover, Reynolds was in the early stages of his highest-profile relationship yet. But more on that later…

After starring in Charmed, Alyssa became very popular both on screen and off. She dated her Charmed co-star Brian Krause for two years until 2003. In 2007, she started dating David Bugliari, who proposed a year later. The pair tied the knot in August 2009. The couple have two children and are still happily married as of April 2020.

There was one woman in the wedding game with Ryan Reynolds even before Blake Lively and Scarlett Johansson. That’s right, Alanis Morissette was engaged to Ryan Reynolds from 2004 until 2007. Their relationship lasted for five years total, but they never went down the aisle. However, Reynolds has declared that he feels like they “were married too.” The couple announced their separation in February 2007. That must’ve been a really tough punch for Alanis. After the breakup, she wrote a song about Reynolds in which she grieved over their former relationship and how much he meant to her. The song “Torch” appeared in her album Flavors of Entanglement, and she admits that she wrote the song for him.

Many have wondered why things ended so abruptly between Alanis Morissette and Ryan Reynolds after being engaged for a handful of years. Since then, the Canadian singer has admitted that she blames herself for things going south. “I get angry at myself for staying in relationships way too long,” she told Women’s Health. However, Morisette also suggested that maybe the two didn’t have enough in common, as well as a potential power struggle between the two towards the end of their engagement.

Alanis Morissette married Mario Treadway, aka Souleye, who is an American hip-hop artist and rapper. They wed in a small, private ceremony at their home in Los Angeles in 2010. They have three children together – the oldest was born in December 2010, then another in 2016, and their most recent baby was born in August 2019. It’s safe to say that her life took a positive turn after the sad break-up with Ryan Reynolds. She deserves nothing but happiness with her husband and her kids.

We all know Ryan loves acting in rom-coms and comedic action movies. So when he starred in Foolproof in 2003, we can hardly say we were surprised. What did surprise us was his on-screen chemistry with Kristin Booth. In the film, the two carry out grand heists together – and we couldn’t help noticing what amazing partners they were. Many fans hoped their chemistry would move off screen. Although some sources stated that their friendship was developing into something “more,” nothing was confirmed. This may have been due to his long relationship with Alanis hanging in the balance.

While many fans of Foolproof shipped a relationship between Kristin Booth and Ryan Reynolds, they would be setting themselves up for failure. This was because Reynolds was in the middle of his engagement to Alanis Morissette. While that didn’t exactly end well, there was no chance that Reynolds was going to jump ship that easily with Booth. Of course, Reynolds’s career has gone in a very different direction compared to Booth’s, but this still begs the question: what is she doing now?

After filming Foolproof, Kristin went on to act in a few more films, including At Home By Myself… with You and The Calling, which was her last big-screen film. When it comes to her love life, Kristin has mostly kept mum. But we do know that she married musician and composer Tim Ware in 2006. They reportedly don’t have any children as of April 2020.

While filming Just Friends in 2005, Ryan worked closely with actress Amy Smart. They had great on-screen chemistry, causing viewers to laugh so hard they cried. The film was a huge commercial and critical success and saw Reynolds play the hopeless romantic Chris Brander who, after being apart from his childhood friend for many years, is determined to make her fall for him. Truth be told, Smart was another female co-star that many speculated was having an off-screen romance with Reynolds. But was it true?

Rumors circulated that the two were more than just friends. Both denied the allegations, of course, and we will have to be satisfied with never actually knowing. Once again though, this seemed unlikely seeing that the actor was in the middle of his engagement to Alanis Morissette. It made sense for Smart to star in Just Friends alongside Reynolds, seeing that she had starred in another successful comedy just a few years prior in Road Trip. But what has Amy Smart been doing since then and where is she now in life?

Since then, Amy has gone on to act in many popular movies including The Single Moms Club and Avengers of Justice: Farce Wars. She has also been seen in episodes of Shameless and Justified. Unlike most people with an active career in Hollywood, she has kept her love life a secret – so we are unsure of her current relationship status.

Ryan Reynolds jumped from one serious relationship to another, with Scarlett Johansson this time. The couple did tie the knot, but they’ve kept the marriage very secretive, away from the red carpet and the paparazzi. They were married for two years. Apparently, the main reason for their divorce was the fact that they had to maintain their relationship over a long distance for much of the time – and Scarlett didn’t love this arrangement. After his marriage ended with Scarlett Johansson, Ryan said that he would never marry again.

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. Since then, Johansson has admitted that her young age during her marriage to Reynolds had a part to play in it not working out. “I mean, the first time I got married I was 23 years old,” she told Elle magazine. “I didn’t really have an understanding of marriage. Maybe I kind of romanticized it, I think, in a way.”

After the marriage ended with Reynolds, the actress started dating French businessman Romain Duriac, from 2014 to 2017. The two had a baby together before they split up – a daughter named Rose Dorothy Dauriac, who was born in 2014 in New York City. Scarlett Johansson started dating Colin Jost in 2017, and they are currently engaged. Looks like Scarlett will be tying the knot again, and hopefully this one will be a keeper.

Back in the day, Reynolds starred in the popular movie Definitely, Maybe alongside Isla Fisher. The romantic comedy had us all laughing and cooing as the two went through their journey of falling in love. Of course, it wasn’t that hard to see the amazing chemistry these two shared on screen. While nothing has ever been confirmed about the two, we can’t help but think they would have made a cute real-life couple.

Isla met Sacha Baron Cohen in 2002 in Australia. They dated for two years before getting engaged in 2004. The two tied the knot in a Jewish ceremony in 2010, and they now have three children. Isla still acts on screen, and has recently been in the series Arrested Development and a few movies including Keeping Up with the Joneses and The Beach Bum.

2011 was the year of love and romance for our guy, Ryan Reynolds. After dealing with the divorce from Scarlett Johansson, he had a few flings before he got together with Blake Lively. One of these was a short fling with the famous actress Sandra Bullock. Sources said that they were acting flirty when they met in Texas in 2011. However, their relationship was presumed to be just a fling, because shortly after Ryan Reynolds connected with Blake Lively.

Sandra Bullock was married to Jesse James from 2005 until 2010. The couple have two kids together. Jesse James was accused of having multiple affairs with different women and checked in into a rehabilitation clinic to deal with “personal issues.” Sources said that they were acting flirty when they met in Texas in 2011. However, their relationship was presumed to be just a fling, because shortly after Ryan Reynolds connected with Blake Lively.

According to People Magazine, Reynolds was seen with the German model Agnes Fischer after his divorce in 2011. Rumors started flying as the two of them were seen together, and many people speculated that they were dating. Sources said that they were acting flirty when they met in Texas in 2011. However, their relationship was presumed to be just a fling, because shortly after Ryan Reynolds connected with Blake Lively.

Besides Ryan Reynolds, we know that Agnes also had a relationship with Shannon Leto back in 2010. Shannon Leto is an American songwriter who’s part of the band Thirty Seconds to Mars. According to various sources on the internet as well as her own Instagram page, Agnes Fischer is not currently involved with any men.

It’s no secret that Ryan Reynolds likes to be surrounded by gorgeous actresses and models. In 2011, he had a fling with actress Charlize Theron – and she was the last woman in Reynolds’ life before he married Blake Lively. According to US Weekly, Ryan and Charlize had different priorities and decided to go their separate ways after dating during the summer months of 2011.

After her brief relationship with Ryan ended, Charlize adopted two children in 2012 and 2015. She has been romantically linked to famous actor Sean Penn, who she became engaged to in 2014. However, they called off their engagement in 2015, just six months later. Since then, Charlize has not been seen with any new love interests, choosing instead to focus on her children and her career. She has been in some big movies recently, including Murder Mystery and The Addams Family.

Blake Lively is an American actress known for her role in the drama Gossip Girl, in which she played the role of Serena van der Woodsen. She met Ryan Reynolds while they were filming Green Lantern, as they were co-stars. At first, they put each other in the friend zone – but pretty soon, their romance started to warm up. Blake is now the lucky wife of Ryan Reynolds, whom she married in 2012. They already have three kids together. They are one of the most endearing couples in Hollywood, and everyone adores them. The family resides in Los Angeles, California.

Ryan Reynolds married Blake Lively on a former slave plantation in South Carolina. Some fans were not too happy after they heard this, but it’s their wedding and they should get to do it however they want, right? This particular plantation also served as the set for the beloved film The Notebook. That might seem romantic, but not so much when you think about the fact that Blake Lively used to date the star of the film, Ryan Gosling. Ironic choice of location, right?

You thought the story ended here, but there’s more. At some point, rumors circulated that Reynolds hooked up with his co-star from Deadpool, Morena Baccarin. Of course, Ryan Reynolds denied the rumors on Twitter, and he and Blake continue to be a happy couple. Unfortunately, being famous and having dated lots of beautiful women in the past tends to attract unwanted attention from the media, as well as unfounded rumors.

After her divorce in September 2015, Morena stated that she was going to marry Ben McKenzie, her Gotham co-star. She was pregnant with their child, a daughter who was born six months later in March 2016. The couple announced that they were engaged late in 2016 and were married on June 2, 2017 – which is also Morena’s birthday. They were wed in New York and are still happily married today.

Monica acted in a Peloton ad called “The Gift That Gives Back” in 2019. It created a lot of controversy after its release on television. In the ad, Monica Ruiz is playing a spouse who gets a stationary bike from her husband as a Christmas gift. After the uproar calmed down, Reynolds hired Monica Ruiz for his Gin aviation commercial. Of course this sparked rumors that perhaps there was more between the two. Both of them denied it. Ryan stated he was just helping a fellow actor in need. His kindness helped her to relaunch her career.

Monica has been married to Christopher O’Malley since 2013. They have two children together – a daughter and a son. While she was pregnant, Monica did a lot of maternity modeling. She also starred in a few commercials. She has kept most of her private life out of the limelight, especially since the unfortunate Peloton ad.

The fans never get tired of inventing rumors about their favorite TV celebrities. The rumors about Reynolds’ impending divorce have been endless, and one of those rumors suggested that Blake got back together with her ex, Leonardo DiCaprio. Fortunately, this was not the case – as they are still happily married. In fact, Ryan always makes fun of such rumors and speculations. Maybe the fans should just relax and be content with the fact that Ryan and Blake live a wonderful, happy life together with their children.