Dean is Rory's worst boyfriend
There's no doubt that Dean has his shooters out there, but I'm not one of them. He simply became far too annoying for my liking, and as time wore on, his presence on the show didn't seem necessary. That might be too harsh on Dean, but I have to be honest. Out of all three of Rory's main boyfriends, he's by far the worst.
But that doesn't mean he treated her badly. As a first boyfriend, and first love, Dean was pretty great. He got along with Lorelai, he was caring and sweet, and he was able to communicate (unlike the other two). He made Rory a car! When it comes to showing Rory love, Dean will have Jess and Logan beat every time. Still, there's negatives to Dean that become apparent with every rewatch.
For all of his amazing qualities, particularly in the first two seasons, there's also an aspect of his personality that's a bit entitled. Yes, he got along with Lorelai, but he could also speak to her (and other adults) in a manner that was disrespectful. Has anyone else picked up on that? Obviously, teenagers don't always have the best filters, so it's realistic, but his tone didn't always match his well-mannered reputation.
Beyond how he conducted himself with others, he often placed so much guilt and jealousy onto Rory that was unfair. I'll never forget the time he left her over a dozen messages and kept showing up at the house. She could have been more open with him about how she was feeling, but I do believe that the way he acted helped push her away... toward Jess.
A big reason for Rory and Dean's second attempted in season 5, I believe, has to do with them wanting to make this work. Their love was powerful, and it was their first go at love. But backsliding into the past wasn't the answer. Even if they hadn't gotten back together, Dean would still be Rory's worst boyfriend. He's wonderful, if not a bit irritating, but he and Rory ultimately grew in two different