‘Gilmore Girls’: Rory and Lorelai Gilmore Didn’t Really Casually Date and Neither Did Anyone in Stars Hollow

Gilmore Girls might not have been about romance, per se, but Amy Sherman-Palladino weaved romantic story arcs in the plot throughout the series. Both Rory Gilmore and Lorelai Gilmore were almost always entangled in romantic ventures. After seven seasons, though, they actually dated a surprisingly small number of people. 

Do you remember everyone Rory Gilmore dated during the original run of ‘Gilmore Girls’? 

Rory Gilmore only seriously dated three people, and she had just two more first dates during ‘Gilmore Girls’ original run. When fans first met Rory, she was just beginning her relationship with Dean Forrester. The romance carried her through her sophomore and junior years of high school. By her senior year, she called it quits with Dean to hook up with Jess Mariano. The relationship ended before she graduated from Chilton.

Alexis Bledel as Rory Gilmore and Matt Czuchry as Logan Huntzberger in Gilmore Girls
Alexis Bledel as Rory Gilmore and Matt Czuchry as Logan Huntzberger in ‘Gilmore Girls’ | Saeed Adyani/Netflix

Once at Yale, Rory had a single first date with a classmate named Trevor, and she agreed to go on a date with Robert to make her love interest, Logan Huntzberger, jealous. Rory and Logan eventually got together, and the relationship carried her through the rest of her college career and the series. Logan and Rory split in the series finale when she turned down his marriage proposal. 

Lorelai Gilmore’s dating history was exceptionally short, too 

Rory must have gotten her penchant for relationships from her mother. While Lorelai once pointed out that Rory wasn’t exactly “dating girl,” neither was she. During seven seasons of Gilmore Girls, Lorelai had five notable relationships and just a couple of unfortunate first dates. 

Lauren Graham as Lorelai Gilmore and Scott Patterson as Luke Danes in Gilmore Girls: A Year in the Life
Lauren Graham as Lorelai Gilmore and Scott Patterson as Luke Danes in ‘Gilmore Girls: A Year in the Life’ | Saeed Adyani/Netflix

Lorelai might have only had five notable relationships during the original run of Gilmore Girls, but she made those relationships count. She was engaged or married to three of those five men. In season 1, she dated Max Medina, Rory’s English teacher. The couple planned to marry. Lorelai called it off at the last minute. Later, Lorelai would settle in with Luke Danes, much to the delight of fans. Luke and Lorelai were also engaged. They also called off their wedding. In the show’s final season, she married and later divorced Christopher Hayden, Rory’s father. 

Sprinkled in between the three men were Jason Stiles, Richard Gilmore’s business partner. Lorelai also dated a businessman named Alex. He inexplicably disappeared. Aside from serious relationships, Lorelai also had a couple of unfortunate first dates. She agreed to double date with Sookie St. James and Jackson Belleville in season 1 of Gilmore Girls. The date was when she had the displeasure of meeting Jackson’s cousin, Rune. In the season 3 episode, “Eight O’Clock at the Oasis,” Lorelai went on a single date with Peyton Sanders, a man she met through Emily Gilmore. Lorelai refused to see him again because he was boring and only talked about his car.

Stars Hollow didn’t seem to have a single serial dater 

Rory and Lorelai called Stars Hollow home. The duo seemed to align perfectly with the town, even in their dating habits. The entire hamlet seemed to have a preference for serious relationships. There wasn’t a single member of the town who appeared to be a serial dater. Even Miss Patty, who everyone characterized as a massive flirt, seemed to prefer serious relationships. After all, she married four times. 

Lauren Graham and Alexis Bledel look at a newspaper while standing next to a mailbox in a scene from 'Gilmore Girls: A Year in the Life'
Lauren Graham and Alexis Bledel in ‘Gilmore Girls: A Year in the Life’ | Saeed Adyani/Netflix

Babette and Morey Dell were happily married. Kirk Gleason dated Lulu and only Lulu. Lane Kim, Rory’s best friend, only had one serious love interest before she married Zack. Even Luke had just two significant relationships aside from Lorelai and a single casual date. 

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