How Many Boyfriends Did Blake Lively Have? Blake Lively Dating History Explored

Blake Lively, who was born on August 25, 1987, was determined to forgo her family’s predetermined career path and concentrate on her college studies. Her brother made sure she went to some respectable auditions, though, and she subsequently made her film debut. Blake sees herself as a “strange combination of incredibly gregarious and really bashful,” and she is also highly particular about the people she chooses to spend the rest of her life with.

Blake dreamed of attending Stanford University despite living in Los Angeles and being thrust into the entertainment industry from an early age because her parents brought her along when they taught acting classes rather than having a babysitter watch her. Blake wanted to simplify her hectic schedule, which included being the class president, competing in a show choir, cheerleading, and being a member of six other clubs.

Blake had already played Trixie in “Sandman” and had landed the role of Bridget Vreeland in “The Sisterhood of the Traveling Pants” by the time she actually enrolled at Stanford.

However, her management requested that she take a year off from school to work in film, so in 2006, she decided to put her studies wait so that she could act in the comedies “Accepted” and “Simon Says,” where Kelly Blatz and Blake first collaborated. Kelly and Blake began dating in May 2004, so by the time they landed their parts on “Simon Says,” they had been together for almost two years. They were close friends since they were young, according to sources close to the ex-couple, so they had a firsthand understanding of what it was like to work as a child actress, especially when you have other aspirations for your future; Kelly actually wanted to be a singer.

Blake also revealed two additional men she had relationships with before she started dating Blatz, but she only briefly addressed them, thus it is unknown how serious those liaisons were: I’ve only ever kissed three people in my life, excluding anything I’ve done for TV or movies. She chuckled during her 2008 interview with Cosmopolitan, “I know—I’m odd!”

At Burbank High School, Blake and Kelly were classmates. Blake even revealed that Kelly had a crush on her, which he was completely unaware of. The marriage parted in April 2007, and Blake suffered greatly as a result. She was anxious that she wouldn’t be able to return to Stanford because of the increasing number of Hollywood projects she was contracted to. Her heart broke because she knew it was too much for her to handle while Kelly was gone working on “The Oakley Seven” and “Zoey 101” and pursuing his musical career with his band Capra.

Kelly stated that he and Blake had been childhood friends and that she was outstanding in an interview with NBC Washington in 2009. I’m overjoyed for her. We occasionally talk, but it’s difficult because she lives in New York,” he remarked of his ex-girlfriend. At the time, Blake had already gained international recognition as “Gossip Girl” Vanessa van der Woodsen for two years. Kelly still gave off the impression that he was more focused on advancing his job than on finding a partner.

Blake and Penn Badgley met on the set of the show for which they were cast, therefore the details of their initial encounter are incredibly unimportant. Blake was cast as Vanessa in the upcoming television series “Gossip Girl,” which is based on the same-named book series by Cecily von Ziegesar, in April 2007. When asked to play Dan Humphrey, Blake’s on-screen love interest, Penn declined, but after the producers failed to find someone who fits the part, Penn accepted.

According to reports, Blake and Penn began dating in May 2007. When “Gossip Girl” fans learned of this, many of them assumed it was just a publicity stunt and had doubts about the reality of their romance. Blake continued to maintain that they were “just friends” in January 2008, saying: “Everyone constantly tries to delve into your personal life or manufacture things that aren’t there. She said that the reports about her having an affair with Penn were absurd.

However, when Blake and Penn were seen having fun together while on their vacation in Mexico, it was clear that they were deeply in love and couldn’t take their eyes off one another. Blake argued that her relationship with Penn was “the happiest I’ve ever been” in an August 2008 interview with Cosmopolitan. “He’s really stoic, quiet, and confident,” Blake said of Penn. Later on, they both acknowledged that they had kept their relationship a secret because they didn’t want to appear unprofessional by combining their working and personal lives. In order to please the show’s producers, they kept their affair under wraps.

While continuing to conduct themselves professionally on the series’ set, Blake and Penn ended their relationship in September 2010. They stunned their “Gossip Girl” co-stars because they had no idea that they were even dating. It was widely assumed that Blake’s desire to have “a lot of babies“—a statement she made in an interview with Allure—was the catalyst for her breakup with Penn. While filming together and portraying the pair in the upcoming seasons of “Gossip Girl,” Blake and Penn carried on with their work as usual. Their admirers were perplexed, wondering if they were in a relationship once more or if it was simply another promotional ploy for the series because they were also seen holding hands and conversing together on the streets. It’s also important to note that in October 2008, while they were still dating, Blake and Penn shared a screen in an Obama campaign ad for MoveOn’s Youth Vote initiative.

blake lively dating history update

In the months following her breakup with Penn Badgley, Blake had a chance encounter with Ryan Gosling, the star of “La La Land,” who at the time was best known for his roles as Lars Lindstrom in “Lars and the Real Girl” and Dan Dunne in “Half Nelson.” After their brief relationship ended, Penn had an affair with Zo Kravitz. They were initially seen hanging out and eating their ice cream in Disneyland. The fan who snapped the pictures claimed they might be a little more than simply buddies after watching them for a time and getting several good photographs. Ryan threw a large party during the film’s Upcoming York premiere in December 2010 to promote his new feature, “Blue Valentine.” Blake remained by his side the entire time. They were later spotted together at the after-party at the Standard Hotel. Blake traveled the globe promoting “The Town,” a thriller directed by Ben Affleck, who also portrayed the character of Doug MacRay in the film, while Ryan was promoting “Blue Valentine.”

Therefore, it should come as no surprise that Blake and Ryan’s relationship ended by the end of January 2011. While Blake was working on “Green Lantern” and “Hick,” Ryan concentrated on his newest films, “Drive” and “Crazy, Stupid, Love.”

After more than six years of dating, Leonardo DiCaprio and Bar Refaeli announced their separation in May 2011, shocking the entire world. For a Lovelace like DiCaprio, there was no time to be alone since he quickly found another woman to fall in love with. It was Blake’s dream come true, more than just an affair: I adored Justin Timberlake and Leonardo DiCaprio when I was a young girl. She admitted as much during an interview with CosmoGIRL in 2007: “They were the two I can truly think of simply being fully in love with.” In reality, it wasn’t the first time Blake had revealed her desire to wed an A-list star; in an interview with Cosmopolitan in August 2008, she also spoke of her concern that Brad Pitt would reject her if he learned she had no dating experience.

Blake, however, first encountered DiCaprio in October 2010 when she attended an audition for the Daisy Buchanan part in the planned Baz Luhrmann production of F. Scott Fitzgerald’s “The Great Gatsby.” Lively lost the part to Carey Mulligan, a British actress, but she left Leo with a strong enough impression that he asked for her phone number and asked her out on a date. When they were touring Cannes in May 2011, they were first spotted together aboard Steven Spielberg’s yacht. Her “Gossip Girl” co-stars were aware of her relationship with the famous Hollywood actor and kept up with it. The project’s executive producer, Joshua Safran, claimed that Blake texted Leo several pictures of the doll she brought to every Los Angeles session. He claimed that she documented her days in a way that was very similar to what people do today on Instagram, but back then there was no Instagram as it is today. How sweet is that?

Leo and Blake spent a lot of time together traveling. They visited Disney World in Florida and spent several days in Australia to meet the adorable koalas they both adore. They were spotted riding a water taxi in Venice, though they didn’t appear to be having much fun and appeared mostly bored, which led many to believe there was a problem between the two. Blake was a superb cook, according to Leo’s friends, and as the saying goes, she entered Leo’s heart through his stomach: he was believed to adore everything she baked, especially bread.

However, no amount of honey cake could stop Leo from looking for models, and their relationship ended in October 2011 so that DiCaprio could rejoin his usual group of friends, the Victoria’s Secret Angels. At the same time, Blake’s “Green Lantern” co-star Ryan Reynolds stated that he loved the meals she prepared and brought to the set for the entire cast.

Ryan Reynolds

Nobody is certain if he said it on purpose to separate Blake from DiCaprio, but it was soon clear that he and Lively clicked.

A year before they began dating, Blake and Ryan initially crossed paths. Lively and Reynolds found it simple to get along during their “Green Lantern” auditions; as a result, their occasional small talk made filming much more convenient for both of them.

Blake and Ryan were reportedly first spotted together in October 2011 while traveling between New York and Boston on the Acela Amtrak train. While Ryan was filming “R.I.P.D.” because he had landed the character of Nick Walker in “R.I.P.D.,” Blake worked in New York, filming for another season of “Gossip Girl.” As they were spotted on the same train once more when Blake arrived back in New York, the couple appeared to have spent the entire weekend together. Later, when they returned there to celebrate their relationship’s fifth anniversary, the couple acknowledged that they first met at the Japanese restaurant O Ya in New York City and thanked the staff for creating “the best food memories.”

A large oval diamond with a faint pink tint was put in the middle of a rose gold setting when Blake was spotted wearing it in June 2012. Later, Blake disclosed that the ring was crafted by her friend Lorraine Schwartz and included symbolic meaning. For Ryan Reynolds, it meant roughly $2 million, and it wasn’t just talking. On September 9, 2012, Blake and Ryan exchanged vows in a private ceremony at Mount Pleasant, South Carolina’s Boone Hall Plantation.

A few weeks later, Ryan expressed regret for their decision to get married there, calling it “stupid”: We will always feel really and unconditionally sorry for it. There is no way to reconcile it. On Pinterest, we had been looking at a wedding venue. When Ryan explained the history of the location to Fast Company, he said, “What we saw after was a site built upon tremendous tragedy. In fact, it was a plantation where many slaves labored and perished.” Blake and Ryan also claimed to have remarried at home, but their erroneous venue selection in 2012 sparked outrage when Ryan was charged with hypocrisy for promoting the film “Black Panther,” which primarily featured African-American actors.

His supporters argued that because he “danced on the bones of their ancestors,” he had no right to argue for the rights of black people.

Ryan and Blake, however, made every effort to minimize the commotion surrounding their error. The pair made a significant donation to the NAACP Legal Defense Fund in July 2020, sending $1 million to the group. They also contributed an unspecified amount to the Young Center for Immigrant Children’s Rights.

James, a daughter, was born on December 28, 2014, when Blake gave birth to the couple’s first child. Since the pair has always been discreet about their personal lives, they kept the entire event’s specifics a secret. Blake and Ryan welcomed their second child, a girl named Inez, on September 30, 2016, after which Blake took two years off from work. She only resumed filming in 2018, playing Emily Nelson in “A Simple Favor.”

Blake and Ryan welcomed their third child, a daughter they named Betty, on October 4, 2019.

Up until the July 2020 release of Taylor Swift’s song “Betty,” the name of their third child remained a secret. Three names were mentioned in the lyrics, two of which, Inez and James, coincided with the names of Blake and Ryan’s eldest kids. As a result, their followers quickly realized that Betty was the name of their youngest daughter. Swift’s most recent album, “Folklore,” featured the song, and Lively and Reynolds both stated that they gave Swift permission to share their daughter’s name on their behalf.

As long as they keep troll-ing together on social media, Blake and Ryan must be content with their union. In 2017, Ryan shared a photo of them wishing Blake a happy birthday, but the image was cropped so that Blake’s face was hardly visible. On Blake’s birthday in 2019, Ryan tweeted ten images of the two of them that they had taken together. The amusing thing about those photos was that Blake had her eyes closed in each one. Lively didn’t wait long to respond to her husband’s trolling, uploading a picture of Ryan Gosling on his birthday instead of Reynolds’. We sincerely hope that their family benefits only from their sense of humor.


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