(Source: news.moviefone.com)
6. She's the only one he felt like he could open up to.
Although teenage Jess had some very real communication issues, which resulted in a lack of closure for Rory post-breakup, the truth is that the two were kindred spirits.

Rory was the only one Jess felt like he could trust when he was forced to move to Stars Hollow and live with Luke –– in other words, his own personal, small town version of hell –– and that kind of thing doesn't just go away overnight.