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Leonardo DiCaprio had many actors vying to play one of his love interests in the 2013 feature The Great Gatsby. One of those actors was reportedly Gossip Girl star Blake Lively. Although she may not have walked away with the role, Lively did end up walking away with the film’s star.

Carey Mulligan beat Blake Lively to star in ‘The Great Gatsby’

Leonardo DiCaprio posing at the premiere of 'Once Upon a Time in Hollywood..' in a suit.
Leonardo DiCaprio | Axelle/Bauer-Griffin/FilmMagic

Lively found herself competing with some of Hollywood’s best actors to star in the contemporary film adaptation of the classic Great Gatsby. The roster of actors Lively had to contend with reportedly included Mulligan, Keira Knightley, and Michelle Williams. Deadline once reported that Lively had lunch with DiCaprio and the film’s director Baz Luhrmann to presumably discuss her hypothetical role as Daisy Buchanan. However, Mulligan proved herself as the right choice for the part after performing her scene-stealing kiss with DiCaprio during her audition.

“I was terrified of reading with him,” Mulligan once told Harper’s Bazaar (via Daily Mail). “But it said in the script that Daisy kisses Gatsby so I asked if I should and Baz said, ‘Yes’ so I kissed him.”

Although Lively missed out on the role, her meeting with DiCaprio reportedly led to a real-life relationship behind the scenes. Lively was one of only a few actors that DiCaprio was known to date. Some other stars that he dated in the past were the likes of Claire Danes and Liv Tyler. Lively and DiCaprio only lasted for five months before going their separate ways. During that time, however, Lively seemed very smitten by the actor. Gossip Girl producer Joshua Safran once revealed Lively went to great lengths to keep in touch with DiCaprio while doing her show.

“We learned a lot from Blake,” Safran told Vanity Fair. “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. 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.”

Blake Lively once shared that people were shocked by the amount of partners she’s had

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Shortly after parting ways with DiCaprio, Lively ended up in a relationship with Ryan Reynolds. Her romance with Reynolds seems to be her last, as she married her Green Lantern co-star just after a year of dating him in 2012. But it seems that Reynolds was one of only a select few of men that Lively officially considered her boyfriend at the time.

Speaking with Marie Claire, Lively confided that the number of partners she’s been with could be counted on one hand. Which couldn’t have been anymore different than the lifestyle of her more adventurous Gossip Girl counterpart Serena van Der Woodsen.

“People like to draw parallels between my life and the scandalous stories on Gossip Girl. I dress the same as my character, so they think, She lives this life on and off set. I recently shared how many boyfriends I’ve had [four], and people were like, ‘That’s impossible!’ But it’s true. I’ve been with very few people. If I’m not with somebody who really excites or inspires me, then I’d rather be by myself,” Lively said.

Some of the familiar names Lively dated before Reynolds are DiCaprio and her Gossip Girl co-star Penn Badgley. But in a separate interview with Marie Claire, Lively explained what made Reynolds her perfect match compared to past partners.

“I knew he would always be my best friend for my whole life. That was the biggest thing to me. I’d never known anything like the friendship that I had with him. I could like him as much as I loved him,” she said.