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Let’s Take a Look into ‘Gilmore Girls’ Stars Alexis Bledel and Milo Ventimiglia’s Romantic History

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Alexis Bledel and Milo Ventimiglia took their “Gilmore Girls” chemistry off-the-screen, sustaining a real-life relationship for almost four years. Although details of their romance remain vague, the twosome remains one of the favorite on-screen couples to date in real-time.

“Gilmore Girls” stars, Alexis Bledel and Milo Ventimiglia flawlessly portrayed the love pair Rory Gilmore and Jess Mariano on the series for almost a decade.

However, more interesting than their on-screen love affair was their offscreen romance which the duo managed to keep lowkey for four years. To date, many still wonder if the duo ever hooked up for real outside the show.

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Alexis Bledel and Milo Ventimiglia | Image: Pinterest
Alexis Bledel and Milo Ventimiglia | Image: Pinterest

Questions like “Did Rory and Jess date in real life?” and “Who did Alex Bledel date in real life?” have especially flooded search engines since the introduction of the Netflix reboot of the series titled “Gilmore Girls: A Year In The Life.”

While their relationship is long over on both fronts, the duo did nurture their romance from 2002 to 2006, with numerous fans still rooting for the favorite on-screen pair.

Wondering what led these favorite Hollywood sweethearts to break up despite their connection on and off the screen? Or perhaps curious for some juicy details about their romance? Continue reading to find out more.


Alexis Bledel and Milo Ventimiglia’s paths crossed when the latter joined the cast of “Gilmore Girls,” in its second season. The actor played Jess Mariano, the newest kid on the block who fast became the neighborhood bad boy.

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Alexis Bledel and Milo Ventimiglia | Image: Pinterest
Image: Pinterest

It didn’t take long for Jess to put a dent in Rory’s otherwise perfect existence. But it was all worth it as the twosome soon discovered their numerous similarities and shared likes, eventually birthing one of the most gut-wrenching love stories in Hollywood history.


As the love blossomed between Rory and Jess, the chemistry between their role players also heightened. In 2002, Bledel and Ventimiglia kicked off their romance in real life, striving to maintain low profiles.

Only a handful of fans knew of their relationship as the two kept things private. Besides a few red carpet appearances, chance photographs, and expressive interviews, there was little to bank on.

Alexis Bledel and Milo Ventimiglia as Rory and Jess on Gilmore Girls | Image: Pinterest
Image: Pinterest

Notwithstanding, marriage seemed like the next step for the twosome, as Bledel admitted in a 2005 interview they already had discussions of going down that road. Sadly, they fell short of expectations, as barely a year after the public revelation, the pair became exes.

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Although Jess and Rory split earlier on in the show due to Jess’s inability to commit, their off-screen counterparts sustained their romance much longer.

In 2006, the twosome called it quits for good, just months before the premiere of the final season of “Gilmore Girls.” In their usual private manner, the pair never revealed details about their breakup.

Alexis Bledel and Milo Ventimiglia as Rory and Jess on "Gilmore Girls" | Image: Pinterest
Image: Unsplash

A representative of the actor confirmed the news saying Ventimiglia was single. However, neither party cited a reason for the split, leaving the public clueless as they relieved the breakup of the all-time favorite Stars Hollow couple all over again. Only, the second time happened in real life, making it more heartbreaking.


Over a decade after their split, the relationship between Alexis Bledel and Milo Ventimiglia continued to make headlines. A 2020 publication on In Style still referred to the pair as the “perfect couple,” just like the characters they brought to life. The author wrote:

“I find no evidence that they are not like the characters they brought to life. Instead, they’re the blank canvases onto which I can project all the hopes I harbored for Jess and Rory, the perfect couple.”

Alexis Bledel and Milo Ventimiglia | Image: Pinterest
Image: Unsplash

The article described their romance as one that resonated because they were a fragment of Stars Hollow that existed in the real world. Little wonder generations of “Gilmore Girls” viewers have been rooting for a rekindling of their romance, albeit in a revival series.


Following their stint on “Gilmore Girls” and ultimately, their breakup, Alexis Bledel and Milo Ventimiglia moved on with their lives.

Ventimiglia went on to date actress Hayden Panettiere from 2007 to 2009. Soon after their breakup, he moved on to talent agent Isabela Brewster. Between 2011 and 2017 he sustained a relationship with marketing coordinator Kelly Egarian.

Rumors of his relationship with “Orange Is the New Black” star, Diane Guerrero swirled in late 2019 after photos of them together on a dinner date surfaced. However, a later report confirmed them as “just friends.”

Ventimiglia has remained tight-lipped about his relationship ever since, leading to speculations that he was single. But his career has been on overdrive as he has continued starring in hit movies.

Meanwhile, Alexis Bledel is happily married to her “Mad Men” co-star, Vincent Kartheiser. They tied the knot in June 2014 and have since welcomed a son together.

Alexis Bledel and Vincent Kartheiser | Image: Pinterest
Image: Pinterest

Despite sailing different boats, there appears to exist no hard feelings between Bledel and Ventimiglia, as they have spoken highly of each other in the last decade. Following Bledel’s 2017 Emmy win for her supporting role on “The Handmaid’s Tale,” the 43-year-old “Heroes” star sang her praise. 

He gushed about how he always believed her a good actress, hence, deserving of a remarkable feat. Looks like there is still some Jess Mariano left in there!

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