15 Secrets Behind Leonardo DiCaprio And Blake Lively’s Brief Relationship

Blake Lively and Leonardo DiCaprio had a whirlwind romance once upon a time, taking onlookers by storm. Hollywood has never had any shortage of power couples – nor of any power couple breakups. The end of the seemingly unstoppable “Brangelina” team of Brad Pitt and Angelina Jolie came as a shock to many fans. Even the strongest of bonds seem to come and go, so it may not come as a surprise that for a few months in 2011, what could have been the biggest power couple of all time happened, then fizzled out of memory just as quickly.

Before Lively met Ryan Reynolds, the future Green Lantern star had a relationship with DiCaprio. While the feeling seemed mutual, the whole thing ended rather abruptly. It all happened so quickly, but the couple had a very impactful relationship.

Before Blake Lively & Leonardo DiCaprio

When trying to understand the steamy affair between Blake Lively and Leonardo DiCaprio, clues might be found in the relationships both were in before they fell in love. For Dicaprio, his most public relationship before Lively was with Sports Illustrated Swimsuit Issue cover girl Bar Rafaeli. Certain details of this relationship reflect aspects of his time with Lively. Outings for the pair included Six Flags and Lakers games – just as amusement parks and pro sports games would set a stage for his time with Lively.

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As for Lively, her relationship with Gossip Girl costar Penn Badgley also had some familiar elements. For one thing, she took her time with him, being friends before dating, and the level of commitment was similar. However, Lively and Badgley were together for three years, while her DiCaprio relationship lasted barely over five months.

The Great Gatsby Audition

The passionate love affair which swept Blake Lively and Leonardo DiCaprio off their feet didn’t happen overnight. The two crossed paths well before they started dating, and even had dinner together a year before the fact (via E Online). It happened soon after Blake Lively auditioned for the DiCaprio version of The Great Gatsby. When they were spotted eating together, speculation had it that Lively had landed the role of Daisy.

Carey Mulligan got that part, so why were they eating dinner that night? Could that have been the first time a mutual attraction sparked between the two? That dinner happened in 2010, and the two weren’t officially an item until 2011. F. Scott Fitzgerald possibly brought these two together. Not bad for an author who passed 70 years before the fact.

Blake Lively Sent Leonardo DiCaprio Doll Pictures

Gossip Girl showrunner Joshua Safran said Blake Lively would text Leonardo DiCaprio photos of a doll to express her innermost feelings (via PEOPLE). “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,” he revealed. The nature of those communications remains unknown, and neither party has ever shared the actual photos.

Without the context of image-based social media, random shots of dolls often seem creepy. However, this was something that Blake felt confident in sending to Leo when they were courting.

Their First Date May Have Been on Steven Spielberg’s Yacht

What made Blake Lively and Leonardo DiCaprio start dating in the first place? Lively wasn’t exactly DiCaprio’s type, and Dicaprio wasn’t the kind of guy that commitment-focused Lively would usually focus on. It may be that context played a role. One of the earliest indications that the two were an item came from an image of the twosome partying on director Steven Spielberg’s yacht (via The Fashion Spot).

A shot of them embracing at a luxurious bash on the floating palace that had powerhouses like Robert DeNiro hanging out was the first clue the stars had gotten together. Both were available, so the timing may have come into play. Getting caught up in the glamour of the moment, it just might have made sense at the time. In any case, seeing as how short-lived the relationship was, they didn’t have the same staying power as other power couples.

Their Venice Escape

With its charming canals and stunning architecture, it makes sense Leonardo DiCaprio would take Blake Lively to this lovers’ hotspot. However, images taken during this outing may hint at early trouble in their relationship. Neither member of the couple look happy while soaring around the city (via Daily Mail).

Lively looked stressed in the photos and DiCaprio looked disengaged. Rumors indicate DiCaprio ended the relationship, but nothing has ever been confirmed either way. Regardless, based on their attitudes in Venice, it isn’t surprising their relationship ended so quickly.

The Big Disneyland Date

Blake Lively and Leonardo DiCaprio had enough childhood spirit left within them to go out on the town together in Disneyland (via E Online). What united them in their love for such stomping grounds? Whatever the case, this trip to the House of Mouse made headlines, but also may give insight into an element of their bond.

This is where you might expect couples who’ve been together for years to hang out rather than during the courtship period – which is as far as DiCaprio and Lively ever got. If there is a case to be made that the Disneyland trip reflected the impulsive nature of their union, it may also be a clue as to why it burned out so quickly.

They Bonded over Koalas in Australia

Another look at the cute side of Blake Lively and Leonardo DiCaprio came when they bonded over koala bears. Continuing their continent-hopping during their exceedingly short-lived relationship, the two A-listers headed Down Under on an Australian excursion (via E Online). This is an outing that makes a lot more sense for the private jet crowd. Why go to a common zoo in San Diego when you can travel to the Southern Hemisphere to see some koalas?

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The couple clearly didn’t always choose the traditional path of celebrity romance. Where other couples might be spotted at VIP nightclubs, red carpets, and major charity events, these two did something kind of refreshing. Seeing two young-at-heart living legends being so childlike is heartwarming. But of course, scenes as beautiful and carefree as this rarely last long in Hollywood.

Eco-Biking Around NYC

Part of being truly young at heart is feeling strongly about idealism in the face of a world that often seems to be falling apart at the seams. When famous people like Blake Lively and Leonardo DiCaprio put such ideals into practice, it is refreshing. On a date in New York City, photos showed the power couple riding eco-bikes around The Big Apple (via E Online).

It’s the down-to-earth nature of this activity that is charming. Finding ways to be carefree in public has to be liberating for those who live constantly under the ruthless eyes of public scrutiny. Still, whatever they shared came and went fast.

Leo Loved Blake’s Cooking

Blake Lively loves to cook and by all accounts, her concoctions are very well received. According to DiCaprio’s friends (via Daily Mail), her ability as a home chef won over a great deal of his heart. It would be ironic if one of the world’s most prolific daters just wanted a housewife. Of course, that’s not how things have turned out.

DiCaprio is still dating in his elite circles, but it might be notable that if a woman really wants to steal his heart, cook him a good meal. On the other hand, it might not be worth the effort because he broke up with Lively, after all!

There’s No “One” For Leo

Whatever did go wrong with Blake Lively and Leonardo DiCaprio, it seemed to take many by surprise. Not only was much of their spirited romance caught on film, but friends and insiders were blown away at how much Lively swept DiCaprio off his feet (Via US Weekly). People close to DiCaprio thought he found “The One.” When their relationship ended, it reportedly threw folks within his circle for a loop.

Never before, the sources asserted, had Leo seemed so smitten. Many were convinced he would permanently turn in his bachelor card after having finally met the love of his life. Alas, it was not to be. Obviously, Blake Lively has since grown up and settled down. Leonardo DiCaprio? Not so much.

Leo’s Victoria’s Secret Type

Most people have a “type” and when it comes to Leonardo DiCaprio, most of his girlfriends fit Victoria’s Secret type. DiCaprio has been connected to several models for the famous brand, including Bar Refaeli, Gisele Bündchen, Tony Garrn. He even was rumored to be dating Gigi Hadid in 2022. That seems to be Leo’s type.

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Dating Blake Lively was one of the few deviations from that trend. However, as soon as that relationship ended, he immediately started dating Victoria’s Secret model Erin Heatherton.

Ryan Reynolds’ Interesting Timing

Blake Lively, in addition to being a stellar actress, is also an accomplished cook. DiCaprio’s love for her cooking was seemingly part of the allure he felt. Right around the same time, Ryan Reynolds also expressed his love for Lively’s abilities in the kitchen (via Cosmopolitan). He went out of his way in interviews to not only talk about how his Green Lantern costar Lively was an awesome person, but how much he loved her baked goods.

Not long after he made these declarations, Lively and Reynolds became a true Hollywood power couple, and they ended up married with three kids and a fourth on the way in 2023. The two started dating within months after Leo broke up with Blake.

Blake Was Still in College When They Dated

There is a fairly decent age gap between Blake Lively and Leonardo DiCaprio, with the actor 13 years older than his ex-girlfriend. In 2011, when the two dated, DiCaprio was 36 and Lively was 23. Lively was obviously an adult, but she was still in school at the time (via OK Magazine). Meanwhile, Leo was closer to his 40th birthday than his 30th.

Lively was studying abroad at the time in France. Part of the logistical challenges was juggling class time along with a huge international celebrity romance. This had to be awkward and their utterly different life stages might have been one of the chinks in the armor of their love.

Ryan Reynolds’ Titanic Shade

When it comes to the Blake Lively and Leonardo DiCaprio whirlwind romance, the effects of those fleeting months may well go beyond the life of the brief relationship. This includes a bizarre performance from Blake’s husband Ryan Reynolds. While promoting the 2018 film Deadpool 2, Reynolds pulled off a very odd promotional appearance. Deadpool “bum-rushed” a Céline Dion performance.

Her song “Ashes” is a featured song in the superhero sequel. The video features Deadpool disrupting her performance by saying “This is not Titanic!” It’s a funny gag, but movie fans can’t think of Titanic without thinking about Leonardo DiCaprio. In that context, the whole performance seems like Reynolds throwing shade at his wife’s former flame.

Life After Blake Lively And Leonardo DiCaprio

The Blake Lively and Leonardo DiCaprio relationship seemed to end as soon as it began. Was it a surprise? Blake Lively takes romance very seriously, never dated much, and landed Ryan Reynolds at a young age. She was more focused on being a domestic partner than a serial dater. But DiCaprio seems to be a perpetual bachelor, and his relationships after breaking up with Lively prove it.

He went back to his Victoria’s Secret fixation, dating the brand’s model Erin Heatherton. That was followed by yet another VS model, Toni Garrn. More models followed, mostly much younger than him. He even had a brief moment with singer Rihanna. He finally seemed to settle down from 2017 to 2022 with Camila Marrone, but they broke up, and he was linked to two different people since then. Lively, on the other hand, has been married for 11 years and has her fourth baby on the way in 2023. She seems happy as a wife and mom. In the end, these two really just weren’t meant for each other.

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