Every Lorelai Gilmore Boyfriend Ranked From "You Made Me A Hoopah" To "Oy With The Poodles"

Few television characters have been as awesome as Lorelai Gilmore and as unlucky in love. The best mom in the world had her share of ups and downs in the romance department. While she only seriously dated five guys over the course of seven seasons, they each left a lasting impression. Everyone has a favorite, but after weighing the guys' personality and chemistry against how they treated Lorelai, I have ranked Lorelai's boyfriends from best to worst.

Trust me, this was no easy task. If I listened to my 'shipper heart this list would look very different, but based on the show, I truly believe this is how Luke, Christopher, Jason, Max, and Alex rank in terms of boyfriend material. How well they knew Lorelai, how in sync they were with her unique sense of humor, and their behavior during the actual dating period all factor in. No matter how gorgeous these fellows are — seriously, Lorelai dated some attractive dudes — none of them were perfect. From secret children to an inability to share a bed, they all had their issues.

So which Lorelai boyfriend was the actual best and which one was she definitely way better off without? Here they are from best, to "kick 'em out of bed."

1. Max Medina

There may not be a better boyfriend on the planet than Max Medina. Rory's English teacher wasn't just swoonworthy, he was thoughtful, he paid attention to everything Lorelai said, and he patiently waited for her to allow him to be a part of her and Rory's life. Max was a kind and smart man. He wasn't as quippy as Lorelai, but he kept up with her as much as he possibly could.

When it came time to ask Lorelai to marry him, he realized he screwed up the first proposal and went all out to buy Lorelai a thousand yellow daisies to make sure the second proposal was just right. The guy even took the breakup as gracefully as possible considering how abruptly Lorelai ended their engagement. He may not have been Lorelai's perfect man, but he was hands down the best boyfriend.

2. Luke Danes

In truth, Luke was a much better pre-boyfriend than he was a boyfriend. He was clearly the guy who got Lorelai better than anyone else. He was able to tell when she was joking and when she was joking to deflect from how she was actually feeling. He was always there for her and he could not have possibly loved Rory more if she had been his own daughter. He fixed broken windows, made Rory special pancakes after her breakup with Dean, drove Lorelai to the hospital to when Richard had his heart attack, and made Lorelai a chuppah for her wedding to another man.

The only reason Luke is losing the number one spot is because as a boyfriend he let his insecurities about Lorelai's parents and Christopher drive a wedge between him and Lorelai, and because of the April incident. Finding out he had a daughter and first not telling Lorelai and later not telling April's mom that Lorelai was part of the package was a huge mistake. Luke is still an amazing man, but he made his share of relationship missteps.

3. Alex Lesman

Alex was only Lorelai's boyfriend for a short time, but boy, the guy could keep up. He shared Lorelai's ambition even if they had vastly different interests. It's true that Alex was little more than a fling, but he was honest, funny, and when he realized how much Lorelai hated fishing he course-corrected so their getaway wouldn't turn into a fiasco.

If only Alex had stuck around longer, he would be higher on the list. Unfortunately, he was out of Lorelai's life before he had to deal with any real drama. While this preserves his awesome boyfriend status, it also knocks him down a few notches because he wasn't there when Lorelai was dealing with any rough patches.

4. Jason "Digger" Stiles

The best quality Jason possessed was his unflinching honesty. He was a weird guy and he embraced his weirdness. He let Lorelai know exactly how he felt about her and why he made the choices he made. As a boyfriend, he wasn't the best fit for Lorelai. Even though they bantered like a screwball comedy couple, Jason's neurosis ran too deep for him to be a good match for Lorelai. She liked eating with a crowd, while he was a private dining room kind of guy. He couldn't share a bed and she was a cuddler.

Add in him going to war with Richard (even though Richard fired the first shot) and it was clear Jason and Lorelai just weren't going to work out. He wasn't the worst boyfriend, but his quirks were ultimately too much for Lorelai.

5. Christopher Hayden

Christopher was Rory's father, but he was also a human tornado. Every time he and Lorelai dated it ended in disaster, largely because Christopher was a total flake. He was never truly there for Rory, he jerked Lorelai around, and even yelled at her in public when she made an effort to be kind to the woman he left her for.

During his temporary marriage to Lorelai, Christopher was jealous of Luke every step of the way. Even though his heart was in the right place and he had a long history with Lorelai that produced Rory, a.k.a. most awesome kid ever, he was never there in the ways a good boyfriend should be. The duo had chemistry to spare, but sadly, it was the highly combustible kind.

At the end of the day, relationships are hard, and it is clear that not all of Lorelai's boyfriends were created equally.

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