Jason ??Digger?? Stiles
[ranking: 13]
Lorelai's short-lived romance with Digger ended with him asking her to choose him over her family, so needless to say, it didn't end well.
Pros: He and Lorelai had some history (summer camp) and he seemed to make her happy... for a little while anyway.
Cons: Literally everything about him was wrong for her, he made her sleep in a separate room because he was a light sleeper, he didn't have a great relationship with his family, and he eventually ruined his relationship with Lorelai's parents.
Marty
[ranking: 10]
Rory found him lying naked in the hall of her dorm and he lived in the friend zone forever after.
Pros: He's a good, down to earth guy who was always kind to Rory.
Cons: He ended up with Rory's college friend, Lucy, and lied about knowing Rory. More Marty
#25 of 51 on The Greatest Fictional Stoners #30 of 85 on List of Oscar-Winning Adapted Screenplay Original Sources
Max Medina
[ranking: 8]
He was Rory's professor at Chilton and Lorelai's first fianc??.
Pros: He seems like an all-around good guy, he proposed with a thousand yellow daisies, and he got along with Rory.
Cons: They were never quite the right fit, they had no chemistry, and he could never really compete with Luke.
Jess Mariano
[ranking: 4]
The bad boy with a brain swept Rory off her feet.
Pros: He loved books as much as Rory, he set her straight when she decided to take time off from Yale, and he could be considerate and caring.
Cons: He had commitment issues, he was irresponsible and disrespectful at times, and he up and left Stars Hollow without saying goodbye.
Dean Forester
[ranking: 9]
Ah, young love. Dean was the cute guy at Stars Hollow High School who eventually became Rory's first boyfriend.
Pros: He was a perfect gentleman, he built her a car for their anniversary, he was Lorelai-approved.
Cons: He was kind of boring (especially when compared with bad boy Jess), and he later cheated on his wife with Rory.
Luke Danes
[ranking: 1]
The original lumbersexual, Luke was the grouchy diner owner who pined for Lorelai for years before they finally got together.
Pros: He made her an ice rink, a chuppah, AND coffee every morning, he gave her money for the Dragonfly Inn, he was the closest thing Rory had to a father figure, he was always there for both of them.
Cons: He let their relationship fall apart.
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