Dean: Seasons 1-3
Dean was a great first boyfriend for Rory. But as far as forever, I don't know how Rory could stand it. He always treated her like a toddler and it really bugged me. He was majorly overprotective. After Rory met Jess I couldn't wait for D&R to break up. And I think the way Dean broke up with her at the Dance Marathon was a little unnecessary and public, huh?
Jess: Season 3
Jess was the boyfriend that Rory had the most in common with. True, he wasn't as good to her as Dean was but he cared about her so much. Even when he comes back in various times during 4-7, you can tell he is in love with Rory.
Dean: Season 5
I definitely liked Dean better during this time. He was much less annoying and let Rory be independent. Even though it was a more awkward situation for them, Lorelei, Lindsay, Luke, and the rest of the town, they tried to make it work.
Logan: Seasons 5-7
Logan was my second favorite. He reminds me more of Jess than Dean in the way that he was a 'bad boy'. I liked Logan and think he was good for Rory. She didn't get into trouble bc of him. It was her fault usually. I can't believe when he proposed to Rory she said no. They'd been dating for like 2 years! Even though I like to think she went back to Jess, if not she can marry Logan. I allow her haha.