Cajanic
The saddest moment for me was after Luke and Lorelai had broken up, and Lorelai was so sad that she called up Luke begging him to come see her.
Of course, that was also the cutest moment when she realized what she had done and tried to get the tape before he heard the message. XD
Just thinking about that scene makes me tear up a little, it was so well done. (God, Lauren is an amazing actress.)
Also when Dean goes to pick Rory up from her party and ends up breaking up with her and she is all surrounded by these other guys. Poor Dean. Just how everything ended with Dean made me really sad. The whole thing with Rory losing her virginity to him and then having that moment go right down the drain was so sad because it was supposed to be something really special for her and it was but in an instant she was slapped back into the harsh reality of the situation with her and Dean not being able to be together.
Another one would be when Chris and Lorelai were 'almost' back together and were so happy and then bam Sherry is pregnant and everything is put back in shambles between them. Man, that hurt. (Even if Lorelai is supposed to be with Luke, it was still really sad.)
I liked Marty so I felt sad for him when Rory didn't want to go out with him.
sad It's always sad to have someone you like tell you they just want to be friends. Poor Marty.
Lorelei needs to stop going to Chris every time she's upset cause she always ends up sleeping with him. When Rory would go to him and tell him not to mess things up between her and Luke that was tough.
crying I like Chris and I think him and Lorelai could have been good together someday but he pretty much messed it up with the Sherry thing, IMHO