Alexis Bledel and Milo Ventimiglia Were the Perfect Couple and I Will Not Hear Otherwise

Their breakup haunted me for a decade.

Breakups That Broke Us: Alexis Bledel and Milo Ventimiglia
Photo: Images

Oddly enough, Jimmy Fallon and I — a young Asian woman from the opposite coast — share a random commonality: a love for Gilmore Girls’ Jess Mariano. The late night TV host proclaimed his Team Jess allegiance when he interviewed Alexis Bledel on The Tonight Show in 2016. Whereas Fallon admitted he had gotten into the series later than most (he asked Bledel to remain mum about spoilers nine years after the show ended, after all), I, on the other hand, have been a longtime devotee of the mother-daughter dramedy — and, in extension, a devotee of Rory (Bledel) and Jess’s (Milo Ventimiglia) onscreen romance that seeped into real life. It’s true: Bledel and Ventimiglia dated for nearly four years despite the deterioration of their TV love. They were, however, intensely private — the day I learned that their relationship had ended in 2006 was also the day that I learned that the actors had been in a relationship at all. I relived the anguish I felt when Rory and Jess ended all over again.

Alexis Bledel Milo Ventimiglia Relationship Breakup
Jason Merritt/Getty Images

I got into Gilmore Girls in high school. The charming town of Stars Hollow was unlike anything I’d ever seen since I grew up in a dense suburban neighborhood in Los Angeles County. Like Rory, I was a bit of a loner and had no desire to connect with other schoolmates; all she needed was her Walkman and her books, and that resonated to the core. While I’m more inclined to forge connections now, I often return to the series when my mental health is in shambles. It’s meditative for me to escape to the small town of Stars Hollow and submerge myself in the lives of the eccentric townsfolk. My love for the series even culminated in the decision to get an “In Omnia Paratus” tattoo (the official slogan of the Life and Death Brigade) in college.

But back to Rory and Jess: I became invested in them the second Jess arrived in town and swiped Rory’s copy of Howl by Allen Ginsberg. Yes, he had his faults; but was he any worse than the adulterous, possessive Dean or the privileged, entitled Logan? It was Jess’s unexpected return in season 6 that prompted Rory to re-evaluate her decision to leave Yale, after all. His transition from troubled teen to published author who rebuilt complicated familial ties cemented his status as the ex with the most growth in my eyes. Then, in Netflix’s 2016 revival, Gilmore Girls: A Year in the Life, Jess emboldened an adrift Rory to write a book about her life with her mother. I mean, is there anything sexier than a man supporting your forgotten ambitions?!

Get the inside scoop on all your favorite celebrities with our FREE daily newsletter, InStyle Celebrity. Breaking news, relationship updates, hairstyle inspo, fashion trends, and more direct to your inbox!

Of course, the young actors were not their characters. Still, Bledel and Ventimiglia’s relationship resonated because they were a fragment of Stars Hollow that existed in the real world — one I often hated to be in. Bledel and Ventimiglia began dating in 2002, a year after Ventimiglia joined season 2 of Gilmore Girls. While their TV relationship met its demise after Jess fled to California in season 3, Ventimiglia and Bledel remained a couple well throughout the series’ run. They were together for three and a half years, but split in the summer of 2006. (Gilmore Girls’ seventh and final season debuted later that fall.) Ventimiglia’s rep confirmed the split to PEOPLE and said, “He is currently single.” Given their remarkably private nature, I learned about the relationship well after the breakup — and the oblivion made the mourning process all the more painful. (But wouldn't it be just like Jess and Rory to keep their private lives under lock and key?)

When Ventimiglia reprised his role in the Netflix revival, it reopened old wounds and led me down a rabbit hole of once was: Their joint stint as 2003 Teen Choice Awards presenters. That goofy picture of them with their tongues out that permanently resides in my iPhone gallery. Bledel’s comments about marriage in People circa 2005 (“It's a fun thing for us to talk about”). In every memento of their relationship (that's available to me online), I find no evidence that they're 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.

While the grief over their split could swallow me whole, I find solace in the fact that they appear to be on good terms — a presumption I’ve chosen to arrive upon despite their innate privateness for my own peace of mind. When Bledel won a 2017 Emmy for her supporting role in The Handmaid’s Tale, for example, Ventimiglia praised his ex in a rare statement and told Bravo’s Daily Dish, “I’m very happy for her. She’s always been a great actor.”

Post split, Ventimiglia dated his Heroes co-star Hayden Panettiere between 2007 and 2009. He’s been linked to Kelly Egarian, a marketing coordinator for Stella McCartney, since 2017. Bledel wed Mad Men’s Vincent Kartheiser in 2014, and the two have one son together. While Bledel and Ventimiglia have long moved on and appear to be at good places in their lives, it’s been more difficult for me to continue on. Some days, I'm fine. Other days, however, I’d glimpse a copy of Ginsberg's Howl and vignettes of Bledel and Ventimiglia appear; and, as Joni Mitchell’s “Blue” fills my head space, I ask myself, “Will I ever know peace?”

Breakups That Broke Us is a weekly column about the failed celebrity relationships that convinced us love is dead.

Related Articles