‘Gilmore Girls’: Chris Pine Almost Played One of Rory’s Boyfriends

Fans of the TV show Gilmore Girls look back fondly on the quirky and beloved characters that made up the cast.

As time goes by, it gets harder to imagine anyone except the actors we know and love playing those parts. But recently Chris Pine let it slip that things almost looked different in Stars Hollow. 

Chris Pine on the red carpet
Chris Pine | Jeff Kravitz/FilmMagic

A home in Stars Hollow

Set in the fictional town of Stars Hollow, Connecticut, Gilmore Girls followed the adventures of single mom Lorelai and her precocious daughter Rory. The pair’s close relationship, along with their witty, rapid-fire conversational style, endeared them to viewers. 

When the show started in 2000, Rory was almost 16, and by the time the final episode aired in 2007, she was 22. During those years, fans got to watch Both Rory and Lorelai do a decent amount of growing up. And as it’s often true, that meant a fair share of failed relationships for both of them.

For Lorelai, her romantic struggles amounted to a series-long crush on Luke, the owner of the town coffee shop, punctuated by ill-fated relationships. But it was Rory’s love life that had the most drama — as you might expect from a teen growing into a young woman. 

The actors that fans remember so well

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Of course, viewers loved the connection between Lorelai, played by Lauren Graham, and Rory, played by Alexis Bledel. But the relationships that still stir up the most discussion are Rory’s three boyfriends. 

Jared Padalecki played Dean, Rory’s first love and all-around good guy. Sadly for him, he couldn’t compete with the bad-boy appeal of her next crush Jess, played by Milo Ventimiglia. Her final boyfriend of the series was Logan, a wealthy playboy who swept her off her feet.

Looking back on the series it seems impossible to imagine any of the three men in Rory’s life looking any different. Dean simply has to have that wholesome appeal, Jess must be dark and brooding, and Logan has to be just a little too charming. The actors that inhabited those roles played them so well that it’s hard to imagine them any other way. 

But one of her boyfriends could have looked different.

Could Chris Pine have been one of Rory’s boyfriends?

Pine has been a heartthrob for years, best known for appearing in movies such as The Princess Diaries and as the young, hot Kirk in the Star Trek prequel. He also made a splash as Steve Trevor in Wonder Woman. He’s been a busy actor over the years, and fans have seen him in a number of different roles. Now they can imagine him in one more. 

In a recent YouTube video interview, Pine revealed that his first professional audition was for Gilmore Girls. He would have been 19 years old at the time, so he must have been reading to play one of Rory’s peers. And with his undeniable good looks, chances are that he might have been cast as one of her boyfriends. When Pine was asked about which role he was auditioning for, he confirmed that likelihood, saying, “I dunno, maybe a boyfriend.”

For faithful fans of Gilmore Girls, it’s hard to imagine ever replacing one of Rory’s boyfriends with someone new. But then again, if those sparkling blue eyes had shown up in Stars Hollow, it would be hard to imagine her resisting his charms. Maybe if the producers of Gilmore Girls can be convinced to bring the cast back for one more reunion show, Pine can join them to play the part he missed out on so many years ago.