He reminds me of Dean, he's nice, but possessive, pushy, clingy and whiny.

He pushed Lorelai to date him even though she was his student's mother, then he pushed her to take him in her house when she had rules about it, then he became whiny when she tried to break up with him which led to their disgusting kiss at school, then he broke up with her because he feel like his career was in danger, really? Why didn't you think of that, man, when you pushed her to date you?

Also, he proposed to her because he wanted to bond her with him after he saw the vibes of love between her and Luke and became jealous, then pushed her to accept his proposal, then yelled at her at her workplace when she wouldn't give him her house key, then became whiny when she told him Rory didn't need him to enter in her bringing.

Also, he ignored all the red flags in their relationship because he was so clingy to her.

Having said that, Lorelai is equally to blame for their dysfunctional relationship from the start.