Blake Lively & Ryan Reynolds: The Romantic Roads That Led to the Couple's Inevitable Intersection at Love and Long-Term Happiness

You always have to kiss a few frogs, even ones named Leonardo DiCaprio, before you find your true prince

By Natalie Finn Sep 08, 2017 8:07 PMTags

It would be so much easier if we were just handed soul mate road maps upon arrival, but alas, more circuitous journeys often have to be made before we arrive at our destinations.

Which isn't to say there aren't special places in our hearts for the people with whom it just wasn't meant to be in the long run—they helped us get to where we needed to go in the end, after all!

And so went the courses of Blake Lively and Ryan Reynolds, seemingly meant to forever diverge until the usual simple twist of fate sent them on a romantic collision course. The parents of two are celebrating their fifth wedding anniversary Saturday, having finally found what they were really looking for in each other.

Blake Lively & Ryan Reynolds: Romance Rewind

For starters, they're both TV turned big-screen stars and underrated actors whose fairly perfect looks have required them to work harder and be doubly smart with script choices in an effort to be taken seriously. Reynolds biggest box office success to date didn't come until last year with Deadpool and call critics regularly shocked when Lively turns in a solid movie performance, even though it's almost every time. (Never mind, ironically, the film on which they met, The Green Lantern.)

They're also both family-oriented (Lively once said Reynolds would make a great "patriarch") and privacy-minded, ultimately keeping their babies entirely to themselves until a grand reveal at Reynolds' Hollywood Walk of Fame ceremony last December that would have made Taylor Swift proud. (Maybe they even discussed it beforehand at Swift's 2016 Fourth of July bash.)

And at 10 years Lively's senior, Reynolds had the oft-required lead time to figure out what he truly wanted, and Lively had enough dating history under her belt to figure out what it is she didn't want anymore.

From Co-Stars to Couples

"I'm actually a very shy person and the idea of losing my anonymity was one that was scary to me," Lively told Vanity Fair recently, recalling the life-changing decision that was signing on to star in Gossip Girl 10 years ago (in 2007, Reynolds was still best known for 2002's Van Wilder). "I remember saying when I read this script, 'Whoever does this will not be able to walk out of their house ever again and be the same as before they started this.'"

The crazy newness of it all perhaps prompted Lively to gravitate toward co-star Penn Badgley, who also played her off-and-on-but-meant-to-be love interest on the show. They quietly dated for almost two years, careful not to seem like more than friends at first (they sat about a foot apart during a joint appearance on The View when the show was a freshman phenomenon), but ultimately their real-life coupling drove fans wild.

And when they broke up, they did not bring their drama to work with them.

"The shocking thing was, I found out on the set of the Season 2 finale that Blake and Penn had broken up months before," Gossip Girl executive producer Josh Safran told Vanity Fair. "They kept the breakup hidden from the crew, which you could never do now. I don't even know how they did it. They kept it from everybody which is a testament to how good they are as actors. Because they did not want their personal drama to relate to the show."

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Lively said that she and Badgley didn't want to rock the boat at work by flaunting their romance on set, or in public, but in hindsight she's guessing that no one would have minded one bit.

"They wanted us all to date," she said. "They wanted us all to wear the same clothes that we're wearing on the show. They wanted that, because then it fed their whole narrative. People could buy into this world."

"If we were photographed walking down the street, [the world] didn't know if it was a paparazzi shot or if it was a shot from the show...At the time, what was heightened was, wow, it all looks similar from the outside, but it's so different on the inside."

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Badgley, who didn't participate in the VF story, has stayed pretty tight-lipped about Lively over the years—and has seemed eager to distance himself from his "Dan Humphrey" days in general. All he'd say in 2015 about the current state of his relationship with Lively was that they mutually didn't have one.

"We haven't spoken in a while, you know," he said on HuffPost Live. "There's an amicable silence, if that makes any sense."

Lively couldn't help but be a little more public when she started dating serial monogamist Leonardo DiCaprio in 2011, a relationship that lasted the Leo Average of about five months.

Fame Pictures

"When I think about shooting the L.A. episodes, Blake was dating [DiCaprio] at the time, and she had this thing where she had a doll that she took photos of that she sent to Leo," Safran, a real font of Lively dating information, told VF. "Blake was way ahead of the curve. It was pre-Instagram. She was documenting her life in photographs in a way that people were not yet doing."

In 2012, Lively played the lady side of a love triangle co-starring the bromantic Taylor Kitsch and Aaron Taylor-Johnson in the gritty crime thriller Savages, and when Access Hollywood asked at the premiere if being involved with that kind of guy at all appealed to her, she insisted no way.

Universal Pictures

"No, no, no, definitely not," she smiled. "That's a little too complicated."

Asked her ideal type, Lively said, "I don't know, I always love somebody who makes me laugh, who's fun to be with." Pressed a little more, she admitted tallness "helps. I'm a tall girl...And I love really high heels. It becomes a problem, sometimes."

Stephen Lovekin/REX/Shutterstock

Well, damn straight Ryan Reynolds is funny. And being 6'2, the 5'10 Blake and her heels are in good hands.

The Canadian-born charmer appears to have had no trouble at least meeting women since he started acting as a teenager. In 1996, he co-starred with Melissa Joan Hart in the Sabrina the Teenage Witch movie, and the 19-year-old actress couldn't help but be smitten.


He gave her a fancy watch for her birthday, she recalled to Chelsea Handler in 2013, and though she thought he was too young for her, "I just grabbed him and started kissing him. You get a piece of jewelry like that, you gotta make out with the guy!" (No, you gotta make out with the guy if he's future Sexiest Man Alive Ryan Reynolds.)


In the late 1990s Reynolds reportedly dated his Two Guys, a Girl and a Pizza Place co-star Traylor Howard for eight months. The documentation on that one is slim (they had to hang out all the time for work, after all), but randomly in 2015, Artie Lange tweeted a throwback pic from when he and Howard starred in 1998's Dirty Work, writing, "Smokin Lead Actress of Dirty Work. Traylor Howard. She was dating 19 yr old Ryan Reynolds."

So, the dates match up.

In 1999 Reynolds coupled up with Third Rock From the Sun star Kristen Johnston at the premiere of The Green Mile.

The actor got serious with rocker Alanis Morissette in 2002, even popping the question in 2004. And while their relationship didn't inspire the Grammy-winning angst that Dave Coulier supposedly did, their early 2007 breakup did fuel her 2008 album Flavors of Entanglement.

Jim Spellman/WireImage

The song "Torch" in particular, was "really about my grief," Morissette told Access Hollywood in July 2008. "I think the most painful, sort of suffering oriented moments in my life [are] when I'm resisting something… If I just say, 'It's true. I'm unbelievably insecure, really broken, devastated,' then I can move through it, toward the next place. But if I keep resisting it, I'll stay there forever."

Reynolds genteelly refrained from talking about his ex (until 2016 when he fairly randomly broke into "Ironic" on Today), but by the time Alanis was out promoting Flavors of Entanglement, he had been engaged to Scarlett Johansson for a couple of months. He and the Lost in Translation star went public as a couple—well, for them, as they refrained from red carpets entirely—in April 2007.


They quietly tied the knot on Sept. 27, 2008, on Vancouver Island. "I never really thought about getting married—it just kind of happened," Johansson told Glamour in 2009, just shy of their first wedding anniversary.

But by December 2009, those 20/20 hindsight signs were starting to crop up.

"We have no time for dates. We work and then go home and—I, anyway—just stare at the wall for a few hours before I go to sleep…Like in any profession, it's difficult," Johansson lamented to Time Out New York. "You want to make sure you have time to invest in your family. It's a challenge, but it's worth it."

Meanwhile, Reynolds headed off to shoot The Green Lantern in 2010, and while he did attend the Tonys that June when his wife scored a nomination (and won!), he and Johansson both made the Comic-Con scene that July but were never seen together.

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In the October 2010 issue of GQ, Reynolds acknowledged that he wasn't much of a chatterbox when it came to his personal life—and had become less of one than ever. 

"Things change when you get married in general," he said. "But in terms of being a couple that's in a public situation and speculated about and all that nonsense, it's changed a little bit. I'm a little more guarded, I think. I'm just a little bit more wary of having my relationship turning into a soap opera. I've unilaterally not addressed it. That's kind of been the fail-safe for me. I choose to remain as private as possible without being secretive."

As their ships-in-the-night before continued, the split rumors only ramped up. And in December 2010, they announced they were separating.

"After long and careful consideration on both our parts, we've decided to end our marriage," Reynolds' rep said. "We entered our relationship with love and it's with love and kindness we leave it. While privacy isn't expected, it's certainly appreciated."

In 2015, when Johansson was remarried to Romain Dauriac (they separated last year), she told Parade, reflecting on why things just don't work out sometimes: "[Marriage] takes a lot of work. It takes a man who's not only confident in the love that you have for one another, but confident in what he has going on in his own career. He has to be in a field that's completely different from yours. My husband's also involved in art. What's important to him is the recognition that he gets from his job, and that has nothing to do with my job."

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So Reynolds rang in 2011 as a single man. Lively, however, was about to embark on her summer of love with Leo, and there were rumors at the time that Reynolds had a brief fling with Charlize Theron while he was waiting in the wings.

At the June premiere of The Green Lantern that year, Reynolds sang his co-star's praises, particularly her cooking prowess (which, coincidentally, was also a rather fetching trait as far as DiCaprio was concerned too).

"Oh, she's quite a baker," Reynolds kinda-gushed to E! News at the time. "There's nothing she can't cook, that's sort of the problem...aren't actors supposed to be out causing massive amounts of bad press and trouble? But this girl's in a kitchen all day, baking our crew on our movie—everything you can imagine. I mean she had soufflés coming! What's weird is she would live 30 minutes away but when she brought stuff it was still warm. I think there's an Easy Bake Oven in her car."

Once again, in hindsight, all the ingredients were there.

David Fisher/REX/Shutterstock

By the end of 2011, Lively was joining Reynolds in Vancouver for holiday time with his family, and they never looked back.

They got married on Sept. 9, 2012, at picturesque Boone Hall in Mount Pleasant, S.C.—an intimate yet glossy affair that was featured in Martha Stewart Weddings.

Private yet public, the couple seemed to relish attending events and even just walking around town as a couple, more so than either ever had before. And there were oh so many places to go: premieres, screenings, the Met Gala, charity events, Canada!

Timing was, indeed, everything.

Rob Latour/Variety/REX/Shutterstock

Lively told Vogue in 2014 (early enough that she wasn't talking pregnancy yet) that she was grateful for every experience Reynolds had before they met, including the romances, because it was all leading up to them being together.

"He's going to be a great father and leader and patriarch—he's so meant to be all of those things," she said. "The fact that he lived so much before we got together, he's the exact realized person that he should be. And so I get to share my life with the person he's become, and we get to grow from there."

Grow they have. They welcomed daughter James—stealthily, secretly—in December 2014. The news of their baby's arrival didn't break for a couple of weeks, and her name didn't get out for another month. The operation surrounding their second daughter's birth last September was a little less covert—but though they brought her to Daddy's Walk of Fame ceremony, they have yet to confirm reports of her name.

But that is just how Blake Lively and Ryan Reynolds roll, and have been ever since they started steadily rolling toward each other.

For more on Blake and Ryan's journey and their upcoming anniversary, tune into E! News tonight at 7 p.m. & 11 p.m.