8. At heart, he's a full-blown romantic.
Remember that one time Jess showed up at Yale and asked Rory to run away with him?! Yeah, us too. #NeverForget

If there's one thing this heartbreaking moment proved beyond all doubt, it's that Jess truly and deeply cared for Rory. He definitely had some issues he needed to work through, but his love for Rory was never the issue. Beneath that brooding and rebellious exterior, Jess was a total romantic.