Maybe Dylan was inclined to idealize relationships. Perfect friendship, true love. When looking from the side at other people, it may seem that they are all fine, great. Maybe he wanted something such as perfect, what makes all these people happy (because they look happy). Since he didn't have a lot of experience (he wasn't at the top of popularity), then it can be represented as it should be. What should be (or can be) is not always what really is. This is when dreams crash against the harsh reality. Although in the case of Dylan, the reality was not so terrible but didn't live up to his ideals.
I wonder what Dylan himself picked on one boy in school who had no friends (except Rachel, who pitied him), making his life even more unbearable. Don't know, maybe he was just relieved that someone was worse than him.
I just want something I can never have.