Everyone loves a good Hollywood love story. We especially enjoy learning about the love lives of some of the biggest celebrities today. Big A-list actor James Franco has not only earned himself a reputation as being one of the best and eccentric talents in Hollywood but also has one of the most interesting dating timelines ever.

The 42-year-old has been through one too many failed relationships and even had relations with other high-profile female celebrities such as Marla Sokoloff and even singer Lana Del Rey. The Pineapple Express actor admittedly has said to publications that he’s “a little awkward and emotionally immature” which often gets him dumped. The news comes as sort of a surprise, given the actor’s A-list status and his good looks. Even in his 40’s the star isn’t great with the ladies, but with his newest girlfriend Isabel Pakzad, Franco may have finally found love.

A Behind The Scenes Look At A Love Story

James Franco has had horrible luck when it comes to maintaining relationships but he’s great at choosing the perfect partner. The 42-year-old dated critically-acclaimed actress Marla Sokoloff during the early 2000s. Sources report that the two struck up a romance after working together on the 2000 film Whatever It Takes. Of course, not all actors fall in love with each other after filming but Franco and Sokoloff certainly did. The couple was living together, up until 2004 when the two called it quits.

Though, Franco and Sokoloff were far from being over when an intimate tape of them leaked online in 2013. Franco told radio show host Howard Stern at the time that the tape was shot when he was a young man and wasn’t at all made for “public consumption.” The Pineapple Express actor describes the video footage as something “innocent” the two made for themselves . . . despite the fact that everyone knew about it. Franco and Sokoloff were an eccentric couple, to say the least.

Franco’s Schooling Was More Important Than Dating

While Franco’s last relationship and breakup with actress Marla Sokoloff was strange, his next one with Ahna O’Reilly was normal. The two started dating in 2006, just two years after Franco and Sokoloff called it quits. Seems like the actor moves on fast. The two seemed compatible with one another, given that they were both high-profile celebrities and actors. The 42-year-old and O’Reilly even worked together on a few projects together. Franco helped direct his girlfriend in Robert Boswell’s Broadway play The Long Shrift. Despite their seemingly great relationship, there were problems going on behind the scenes.

In 2011, the two ended their five-year-long relationship. Franco himself, reportedly spoke with Playboy Magazine about the break-up, noting that his continued education commitment from Yale University, Warren Wilson College, Brooklyn College, and then Columbia University had been the last straw for Ahna O’Reilly. We’re pretty sure there was more to the story than either led on but clearly weren’t willing to spill the beans in the end.

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Rumored Relationship With Lana Del Rey

Clearly, Franco likes the idea of love but isn’t very good at putting it into practice. Franco has been caught up in dating rumors for years. Perhaps the most interesting piece of his long-list of rumored relationships is with singer Lana Del Rey. Back in 2015, the two posted selfies of each other on their Instagram pages and Franco even helped promote her upcoming 2015 Honeymoon album. The 42-year-old even published a poem in V-Magazine that was entirely about the singer. To say that the actor has admiration for the singer is an understatement.

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The This Is The End actor once told Howard Stern on The Howard Stern Show that they were just friends. Though, Franco did admit that he “would have sex with her music.” That’s a rather suspect statement. Lana Del Rey has also responded to the dating rumors, noting that she "looks up to the actor," all while confirming that they are indeed just really good friends. Sometimes friends fall in love, though.

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Is She His Future Mrs. Right?

James Franco may not be great at love, but it seems he’s finally found Mrs. Right. The This Is The End actor has since moved on to actress and film producer Isabel Pakzad. When it comes to picking very accomplished women, Franco certainly excels in that department, as Pakzad is the film producer of the 2020 film Birds of Prey: The Emancipation of Harley Quinn.

The two have been spotted on outings together and aren’t afraid of showing lots of PDA for the world to see. They’ve been dating since November 2017 and despite everything, including sexual allegations made against Franco back in 2018, they’ve remained inseparable. US Weekly even reports that despite the couple's endless-Honeymoon phase, they’re getting quite serious and are even “considering getting engaged.” James Franco has been in year-long relationships before, let’s just hope this one is the charm.

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