Ryan Reynolds Pushed a Playboy Lifestyle That Inspired Break-up Anthems and Almost Ruined His Career

Thu Mar 24 2022

Ryan Reynolds is a dreamboat that graces the dreams of gorgeous women worldwide. It turns out, that more than a few famous women graced the actor’s arm… and his bedroom. They’ve all succumbed to the same sexiness that is somewhere between stunning and charming, something few stars possess as much as Reynolds.

Before finding the love of his life, actress Blake Lively, this frog had to kiss a ton of princesses before finding the one he would build his life with. From Scarlett Johansson to Agnes Fischer, Reynolds has been around the block and sampled some of the finest and most dramatic women in the spotlight.

The Road to Blake Was Long and Winding

Many people see the love story between Ryan Reynolds and his wife, actress Blake Lively, as one of the sweetest of all time. You wouldn’t be wrong to believe they’re lucky to have found each other, but you’d be fooling yourself if you believed this was Reynolds’ first stab at marriage.

Reynolds not only had a romantic history with several other celebrities, but he also has exchanged vows with at least one of them. That’s right, marrying Lively was not his first jaunt down the aisle to happily ever after – he thought he’d had that before, but he was mistaken.

Reynolds Climbed to the Top With a Little Help From Previous Girlfriends

Though he has reached acclaim through his own merit, Reynolds certainly spent the early days of his career riding the coattails of his girlfriends. They were mostly actresses of higher acclaim than him, as well as a few models here and there.

Each relationship taught Reynolds something different about how adult relationships, whether casual or serious, manage to be healthy and successful. Wow, they really managed to whip this playboy into shape throughout the years. Thank goodness for them!

He Dated Melissa Joan Hart

Before Sabrina the Teenage Witch was turned into a hit TV show, it was a major teen movie. Ryan Reynolds starred alongside his future lady, Melissa Joan Hart, and knew that he was instantly smitten. He would do anything to be with her.

He courted her with all of his might and despite a slight age gap, Hart knew she couldn’t stay in a relationship with someone under the age of 18. She knew their relationship likely had a timeline and was not really up for hanging around for him, but they still had some fun together.

Ryan and Melissa’s Love Story Ended Quickly

The Sabrina, the Teenage Witch stars had a slight age gap between the two, with one party teetering on adulthood and the other already experiencing adult life. Hart was 19, while Reynolds was only 18, and while it wasn’t quite problematic, she saw some roadblocks.

Though their relationship was short, it wasn’t lacking steam. She recounted, “He was 17 and I was, like, 19,” she said. “I was like, ‘You’re too young for me.’ So I stopped his car . . . and I wasn’t sure; ‘am I gonna get mad at him?'” She went on, sharing, “I just grabbed him and started kissing him. You get a piece of jewelry like that, you gotta make out with the guy!”

Reynolds Dated Alanis Morissette

Not only did Reynolds date Morissette, he was even engaged to her. The two Canadian stars started dating in 2002, and were engaged in no time at all. However, their engagement was a long one, lasting more than 3 years. They were engaged for longer than they had even been together.

Their relationship bloomed after getting engaged and they eventually realized that they loved each other but they weren’t capable of keeping their relationship alive. They needed to be able to stick together through it all and they weren’t super capable of it.

Did He Inspire Alanis’ Work?

Morissette was moved by her relationship with Reynolds, so moved that she reportedly was even inspired to write her next album about him. She knew that she was not about to spend the rest of her life with the wrong person, which might have been the case with Reynolds.

Reynolds is the supposed inspiration for her album, Flavors of Entanglement. Before her obsession with Dave Coulier began, she wrote some of her best work while cheering up after her breakup with Reynolds. Her 2008 album also included the song Torch, which was supposedly inspired by him.

Betty Makes a Pass

Actor Ryan Reynolds has dated many of Hollywood’s elite, but there are some who expressed their interest in him that he certainly missed out on. Notorious flirt, Betty White, seemingly set her sights on the gorgeous Canadian actor we see before us.

Though they didn’t appear to advance past a few flirtatious comments and whatnot, they clearly had a chemistry that could not be ignored. We wouldn’t be as surprised if someone told us that Ryan thought something was there, she was an American treasure, after all.

He Dated Rachel Leigh Cooke

Reynolds had spent some time under the radar cozying up with actress Rachel Leigh Cooke. Reynolds and the Josie and the Pussycats star were infatuated with each other, but they kept their romance more private than some of her other relationships.

Reynolds followed in the footsteps of Rider Strong, Antonio Sabato Jr., and Daniel GIllies – some of Cooke’s other high-profile relationships. She certainly had her pick of the litter, and Reynolds probably knows just what he’s missing out on.

3rd Girlfriend From the Sun

In 1999, following his public breakup with another celebrity of his same status, Ryan Reynolds dated actress Kristen Johnson. They were hot and heavy for a while, appearing on each other’s arms at assorted red carpet events amongst other things.

These two never really got too serious. The 3rd Rock From the Sun actress cozied up to the apple of her eye following his breakup with Traylor Howard. Things got private between the two, with a few public appearances here and there to make things seem like a bigger deal.

He Was Married to a Dime

Many people forget that before he belonged to Blake Lively, he had promised forever to Scarlett Johansson. It turns out, though, that forever had an expiration date. After splitting up with ex-girlfriend Alanis Morissette, he found himself keeping this Academy-recognized actress company.

ScarJo had just broken up with Josh Hartnett, and the two quickly got involved after their breakups, as if to soothe the pain of a long-term relationship coming to a close. The two married quietly in 2008, after getting together in 2007. They didn’t skip a beat.

They Were Married Relatively Young

When looking back at her earliest relationships, ScarJo reflected candidly. She shared, “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.”

It was with this, of course, that she was describing her previous marriage to Reynolds. Little did either of them know, this relationship experience would help manifest in some of the best work she had done in her career. What was the project that she channeled her heartache into?

Their Divorce Guided ScarJo in Her Later Performances

Scarlett Johansson later channeled her divorce experience into her performance in Marriage Story. Luckily, though, not everything has been so negative between the two since they split. She divulged some secrets that she learned while married to the actor, key defining characteristics for anyone dating in Hollywood.

“The logistics of being with another actor are challenging. There has to be a real understanding of how you share your time, especially when two people’s careers are going at the same rate. Or even if one person is more successful than the other, that also proves challenging. There may be a competitive thing,” she shared.

His Relationship With Sandra Bullock Started on Set

Who would have thought that an onscreen romance would turn into the real thing? Oh wait… that happens a lot, apparently. Anyway, his relationship with Sandra Bullock was short and sweet, but certainly not far from the spotlight by any means.

When Reynolds and Bullock got together, he was in a tough spot with his marriage ending not long before the two got together. They struck up a romance on the set of The Proposal, and we’re still a little shocked that it didn’t end in an actual proposal.

Sandra Robbed the Cradle

The two dated with a pretty big age gap between them. Sandra Bullock was 12 years Reynolds’ senior and she was happy to take it as it was: a relationship open to a world of responsibilities. She could be with anyone, as could he, yet they still chose each other…

Or, they chose each other in the moment. Unfortunately, their love did not last. Reynolds was still pretty fresh out of a marriage and needed to make sure that he didn’t get way too ahead of himself just after ending one of his most important relationships. These two didn’t last.

Hooking Up With Co-Stars

Back in the late 1990s, Reynolds appeared in Two Guys, a Girl and a Pizza Place. While on the show, he found himself getting comfortable with his co-star, Traylor Howard. He was infatuated with her and suddenly, her opinion meant absolutely everything to him.

Rumor has it, Reynolds had a really hard time getting over Traylor. She had some kind of hold over him that he really could not resist. She was the apple of his eye, until she broke his heart. Their relationship, which started in 1998, ended after eight months together.

He Dated Charlize Theron

Ryan Reynolds also dated South African-born Academy Award winner, Charlize Theron. The two were set up by mutual friends who thought that it might be a good fit for them, however, it seems they had different priorities at the time. They just wanted different things.

These two shared a two-month fling during the summer of 2011. Reynolds reportedly only wanted something “casual,” standard male-speak for something non-committal. She’d reportedly been “rushing” to settle down – it was quickly clear he wasn’t going to be that person for her.

He Cozied Up to Tara Reid

Some might say that anyone dating Reid at the time was fooling themselves to think they were the only one she was involved with. Reid had stolen so many hearts over the years, but being serious with them was not the name of the game in her eyes.

Of course, he found himself wrapped up in the mix of Tara Reid’s flirtatious mojo. The two cozied up between takes on the set of National Lampoon’s Van Wilder. They got fit and flirty together, raising a lot of eyebrows about the nature of their relationship.

Together in the Public Eye

Tara Reid and Ryan Reynolds were close and comfortable enough with each other that they made several public appearances together, such as hosting TRL back in the day. However, these appearances weren’t official relationship business, they just stirred the pot.

As it turns out, Reid’s had a pretty active love life with high-profile celebs other than Reynolds. He was just one of many, including rock star Tommy Lee, Michael Axtmann, and Michael Lillelund. She claims to have married a couple of these figures, though they deny those claims.

He Found What He Was Looking For

When Ryan Reynolds met Blake Lively, he knew it was truly game over for him. There was no one else he would like to spend his time with as much as her. He was instantly smitten with this gorgeous celebrity, who was roughly 11 years younger than him.

Lively and Reynolds met on the set of Green Lantern back in 2010 but they were both committed relationships with other people at the time. They were both single by 2011, and barely took a beat before deciding to explore their relationship together.

It All Started at Comic Con

Lively and Reynolds began their love saga after their first appearance on stage together at Comic Con. She was dating Gossip Girl co-star Penn Badgley, and he was still married to ScarJo at the time. They still had an instant, undeniable attraction.

However, before the two started quietly dating, Lively had another A-list man on her arm. Lively had a summer fling with Oscar-winner Leonardo DiCaprio, and in the months following, she started to get extra comfortable with her next beau, who would end up becoming her husband.

Their First Date Wasn’t Really Meant For Them

The two went on their first date in the fall of 2011, however, they were actually on a double date – each on a date with someone else. They knew they had clearly been set up with the wrong person, and felt they had met their match with each other.

“We were buddies then. I remember it was funny because, for about a year after Green Lantern had come and gone and all that stuff, we were both single. We went on a double date. She was on a date with another guy, and I was on a date with another girl. That was the most awkward date [from their perspective] probably because we were just like fireworks coming across.”

Did His Flirting on Set Stop When He Got Married?

In the simplest terms, he did not give up the game when he tied the knot with Lively. Though the world knows the two as a super couple, always trolling each other on the internet, his onscreen chemistry has proven to constantly be the result of that.

In 2019, there were rumors that Reynolds had strayed from his wife and that they two had been living separately for a time. A source told Ok! Magazine that “there were days Ryan was in L.A. alone, surrounded by God knows who, while she was home taking care of the kids.” Well, they somehow managed to overcome it.

They’ve Been Popping Out Little Munchkins Together

Marriage is, of course, a journey. These two have toughed out even the hardest of times, and have come out stronger as they continue to grow their family together. Relationship ups and downs happen to the best of us, and these two didn’t want to let that get in the way of their family goals.

Now, they’ve seemingly worked through their woes, leaving them to build the family they have always wanted. Now, they’re proud parents to three gorgeous little munchkins. They’re so proud to be parents to James, Inez, and Betty Reynolds.

He’s a Family Man Now

Ryan Reynolds has truly found his match with Blake Lively, so we love to see new tiny humans spawning from this gorgeous family. It seems that there has been one significant piece that really whips the Deadpool star into shape: his family.

It’s clear to us that Ryan Reynolds needed to experience everything possible in the world of romance before he could settle down and become the dad we all know he is. Now, his role as a father is possibly his best credit yet. He’s really got his own awesome method.