I love GG. I'm a big fan but with that being said, there are some things that annoy me just like many other fans. Just a couple of thoughts when I watch the series:
1. I think my biggest problem with the series is that it's frankly a little snobby. I understand the entire premise was originally based on small town Rory going to a new world in an elite private prep school in New England and Lorelai has to reconnect with her stuffy but privileged roots but there were just a few too many things that made it hard to empathize for most people. I feel like they blatantly insulted all public school kids as not only not as smart but just completely apathetic towards their education and Rory was just too good. They act as though without Chilton, she never would have been able to amount to anything in life. While attending a school like Chilton paves the way for Ivy League schools, I think Rory could have survived attending a state college or another prestigious private school. As we know from a YITL, Yale-educated Rory still ended up becoming unemployed and lost which is exactly what they feared. Not saying that Rory shouldn't strive for Harvard but the reality for most teenagers and their parents is that they would love to attend these schools but they just can't. Yet they still make it in the world. My biggest disconnect from the real world was when Lorelai was going to buy the inn because she couldn't produce the money. Rory's solution is to simply call up Grandma and Grandpa for the money and then run to mom with the exciting news. Boom! Done! Once again, having rich relatives affords them things that most people simply have to go without. I understand sometimes people just have more but for the average person watching, it was just a little too perfect to be relatable and for little girls watching Rory and dreaming of going to Harvard and not being the community college failures Lorelai refers to, they might not understand why most parents and grandparents can't just produce those things. Not a great lesson to pass on.
2. Speaking of rich privilege, I flat out couldn't stand the character of Logan. I understand that by going to Yale, Rory was going to meet some sophisticated guy who would sweep her off her feet. I just don't understand why Rory was so swept off her feet. I guess I just wanted her to stay season 1 Rory a little too much but I don't get why a humble girl from an average home is truly taken by the rich playboy. Maybe she'd be drawn to the money and flash briefly but then move on. Sure, Logan eventually falls in love with her but not before he acts like an ass first and is still just a rich kid who thinks he can rule the world with his money. I just never found him to be a likable character. I was rooting for Jess when he actually pointed out to Rory how Logan wasn't a good guy and steered her wrong. With Logan, she was always wowed by his crazy stunts but it never felt like it was really Rory. This was even more true with YITL when he's giving her the fun and sexy affair but none of the actual intimacy and commitment. It made sense that Rory would turn to him when she was lost in life because he was never right.
3. Pretty much Lane's entire story line was awful. I loved her fun, unique character and was so excited to see where she went. While I liked the character of Zack, I don't know why they couldn't have just had a sweet love story and band adventures. I don't see why Lane had to end up married with twins and no secure source of income or career at 21 or 22. Just my two cents. They could've had a kick ass girl like Lane hitting the road and trying to make it big with music and meeting all kinds of crazy and interesting characters. She wanted to be a rock star and get out from her mother's eye so why would she immediately settle down? I understand she fell in love but she was given no time to actually grow up and explore her life. Seems like the writers just had no thoughts on her. I also found it hard that even while liking music, her mother wouldn't have pushed for her strictly raised daughter to go to college. Plenty of college kids also play in bands.
4. I think Rory and Dean's affair was almost a necessary part of the story. It needed to show Rory making a very real and human mistake and to show that not everything works out perfectly. At the same time, it was again weird that an 18 year old Dean got married in the first place. Not trying to judge and it happens but didn't really need to. Seems like an 18 year old guy would also want to go to college or explore life more and grow up instead of accepting odd jobs around town and playing house. I'm not sure why they had to portray Rory as the only girl in Stars Hollow interested in or able (or even smart enough) to go to college. They also could've done more to make Lindsay a little less one-dimensional.
5. And of course Luke's daughter was just a stupid, unnecessary story line that added nothing to the show.
I could probably think of more but those are the ones that have always stood out to me. Again, I love the show I just think a few things stood out as unbelievable or unlikable. I also have plenty of opinions about AYITL but I'll spare you for now.