Rory crying over logan
That scene at the end of s5 ep 18, where drunk rory was crying over logan on the bathroom hits way more different after you experience it yourself.
The first time I watched the show I was just starting high school and I've never truly had feelings for anyone, so that scene didn't strike me in any way.
But near the start of college, I was watching it again but i really felt this scene this time. Not too long ago I secretly had the feelies for a guy but he was such a player and was with a different girl basically every week (thank god I got over him eventually lol). I was pretty good at playing it cool in front of him, but I distinctly remember reaching my breaking point one day, coming home, and basically sobbing for an entire evening. That's when I realized this was going no where and let go of the whole thing.
That was all near the end of high school, and I think I blocked that evening out of my brain, until I rewatched gilmore girls and saw this scene. Oh man, that brought me back. But I'm glad I had that experience, because I think it helped me raise my standards.