Milo Ventimiglia’s Romantic History: A Timeline Of His Girlfriends – Hollywood Life

Milo Ventimiglia’s Romantic History: From Ex Girlfriend Alexis Bledel & Beyond

While Milo Ventimiglia has never married, he's dated some of Hollywood's most beautiful women. We've got the 'This Is Us' star's romantic history.

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Milo Ventimiglia
Image Credit: AP

Milo Ventimiglia remains one of Hollywood’s most eligible bachelors at the age of 43. While the This Is Us star is currently single, he’s dated several of his stunning TV co-stars over the years. The handsome actor gained fame as bad boy Jess on The Gilmore Girls in the early and mid aughts, before continuing his TV career on NBC’s Heroes. A whole new generation now knows him as Jack Pearson on NBC’s family drama This Is Us, where he has been helping make audiences bawl their eyes out since 2016.

While Milo has dated some high profile co-stars, he has always preferred to keep the nature of his love life as private as possible. “I try to minimize myself so people can see the character and can really dive into the work,” Milo told People in Dec. 2017, adding, “I try and remain as anonymous and invisible as I can so it doesn’t take away from the experience of the men that I play. I don’t know how interesting my life is any more than anyone else’s.” Here’s the rundown of all of Milo’s loves.

Alexis Bledel

Milo Ventimiglia and Alexis Bledel
Real life sweethearts Milo Ventimiglia and Alexis Bledel in a scene from ‘The Gilmore Girls’ episode ‘Lorelai’s Graduation Day.’ Photo credit: The Everett Collection.

Milo and Alexis Bledel met on the set of the CW’s The Gilmore Girls, when he played her love interest Jess Mariano. Though Rory and Jess’s dating history was cut short by too many outside forces on the show, the pair had a long relationship in real life. Milo and Alexis dated for four years, officially becoming a couple in 2002 before calling it quits in 2006.

Alexis, 39, went on to marry her Mad Men co-star Vincent Kartheiser in a secret 2014 wedding ceremony. She and Milo would meet up on screen once again in 2016’s Gilmore Girls: A Year In The Life revival for Neflix. Milo continues to respect his ex’s acting chops, especially after she won an Emmy in 2017 for The Handmaid’s Tale. “I’m very happy for her. She’s always been a great actor and I think as long as she’s been in the business for her to be recognized,” he told The Daily Dish.

Hayden Panettiere

Milo Ventimiglia and Hayden Panettiere
Milo Ventimiglia and Hayden Panettiere dated for two years from 2007-2009 while co-starring on NBC’s ‘Heroes.’ Photo credit: AP.

Milo once again fell for a co-star when he began dating actress Hayden Panettiere  in 2007, when he was 29 and she was just 18. They met on NBC’s Heroes, which ran from 2006-2010. Though his Peter Petrelli and her cheerleader Claire Bennet didn’t really cross paths and definitely didn’t have a relationship on-screen the way Jess and Rory did, the couple wasn’t afraid to show their romantic feelings in their two years together.

Hayden was Milo’s most high profile romance, as they attended a number of red carpet events together. Even on set, the paparazzi managed to get photos of the hunk and the starlet making out in front of their trailers. Upon their split in Feb. 2009, Hayden, 31, began dating then-world heavyweight boxing champion Wladimir Klitschko, 44. They broke up in 2011 before getting back together for another five year stint between 2013–2018, which produced a daughter Kaya Evdokia Klitschko in 2014.

Isabela Brewster

Milo Ventimiglia and Isabella Brewster
Milo Ventimiglia and Isabella Brewster briefly dated from late 2009-10 following his split from Hayden Panettiere. Photo credit: AP.

Milo was briefly linked to The Fast and the Furious actress Jordana Brewster‘s younger sister Isabella in late 2009 into early 2010. The actor and the talent agent were photographed getting cozy in Santa Monica, CA on December 20, 2009, as Isabella put her arm lovingly around Milo. But the ultra private actor immediately stood apart from her once he spotted the paparazzi zooming in on their date.

Milo and Isabella headed to the Happiest Place on Earth — Disneyland! — for a February 21, 2010 romantic date where he was photographed planting sweet kisses on her forehead while putting his arm around her waist. The two even wore matching mouse ear hats! Eventually their brief relationship ran its course and Isabella went on to date British comedian Russell Brand. She later married former NBA star Baron Davis in Jan. 2014.

Kelly Egarian then Diane Guerrero

Milo Ventimiglia and Diane Guerrero
Milo Ventimiglia and ‘OITNB’ star Diane Guerrero were briefly linked after having a romantic lunch date in Oct. 2019. Photo credit: AP

Milo’s most recent relationship was with Stella McCartney brand marketing coordinator Kelly Egarian from 2016-2017. They were first  photographed holding hands during a Dec. 2016 lunch date in Venice Beach, CA. Kelly attended the 2017 Prime Time Emmys with first time nominee Milo, but she did not walk the red carpet as his date. Instead, she sat with him inside during the ceremony and at the post-ceremony dinner.

The last woman Milo has been linked with is Orange is the New Black star Diane Guerrero, 34. In early Oct. 2019, the pair was photographed having lunch together at Los Angeles’ Mexican restaurant Escuela Taqueria, then headed nearby for dessert at The Milk Shop. It was later reported that the two were just friends, and Milo continues to be tight lipped and private about his love life.