Rory vs. Serena
Rory: Good-natured girl who had a few unfortunate run-ins with the law -- she crashed a yacht and devil-egged Jess's car. And she had trouble ditching her dopey high school boyfriend. She even hooked up with Dean after he got married. Spends her life wanting to go to Harvard, but is convinced to go to Yale because of her grandparents.
Serena: A little bit of a wild child, but sweet at heart. She's done a lot of drugs, and thought she murdered a guy for a while. Is also hung up on her stupid high school boyfriend, who she keeps going back to, even though she could do so much better. Has plans to go to Brown but is convinced to interview at Yale because of the Dean's invite and a slightly vindictive streak.
Verdict: Both are pretty girls, with some issues, but Serena would be more fun to hang out with.

Lorelai vs. Lily
Lorelai: Hot single mom raised in a wealthy family, but shuns the rich lifestyle. Hung up on her first love/father of her child. Keeps going back to him, even when she's dating and committed to someone else.
Lily: Hot single mom who is wealthy and will do anything to stay that way. Still stuck on her first love Rufus, even though he's even more dopey than his son.
Verdict: Lorelai's more laid back, but Lily's got the better wardrobe.

Dean vs. Nate
Dean: He's sweet, loyal, would give you the shirt off his back, but he's a small town boy, and out of the loop when it comes to worldlier issues. He likes his quiet life and is awkward around people with money.
Nate: Comes from a well-off background, but he's kind of uncomfortable about the status that comes along with his position, but he's a loyal friend and stays to the sidelines of the messier girl issues that abound.
Verdict: This one is a tie. Both very pretty. Both would be great if they just didn't ever talk.

Paris vs. Blair
Paris: She gives uptight a new name. She's no-nonsense and beyond driven and is focused and determined to get her way, even if she has to step on the little people to get there.
Blair: She's a totally prissy queen bee, who rules the school with sophistication and grace. She's smart and savvy and will let nothing stop her from meeting her goals, and not only will she step on people, but she'll crush their dreams, ruin their hopes of a future and cause them massive amounts of embarrassment and pain. But yet she won't break a sweat while doing it and she'll be dressed outrageously to boot.
Verdict: Paris would hate and want to be Blair all at the same time.

Chilton vs. Constance Billard
Chilton: The Hartford based school had cute uniforms and was hard for a new girl to weather, but despite some competitiveness, there wasn't a pack of vicious mean girls out to eat an eager studious teen alive.
Constance Billard: Gorgeous location in New York City, amazing education, cute uniforms, offers a leg up for college, but is insanely tough for a fish out of water like Jenny to manage.
Verdict: Chilton. Not only were the kids nicer there in general, but it has the leg up since it was co-ed.

Logan vs. Chuck Bass
Logan: Born rich, likes to throw wild parties, girls throw themselves at him. Lives the life, runs a secret underground club at Yale. Is a risk taker. A total player, but would throw it away for the love of Rory Gilmore.
Chuck Bass: Born wealthy, full of himself, loves to party, indulges with many women. Enjoys flaunting his wealth and wearing insanely awesome clothes. Wants to be in a secret underground club at Yale. Loves the ladies, but can't kick his feelings for Blair Waldorf.
Verdict: Tough one, but we're going with Chuck Bass. Because he is Chuck Bass after all, and the scarf. The scarf earns bonus points.

Stars Hollow vs. Upper East Side
Stars Hollow: Small quiet town, out of the way of a lot of distractions, but filled with a bunch of eccentric characters who were always sticking their noses into other people's business.
Upper East Side: In this exclusive well off little bubble that the van der Woodsens, Basses and Waldorfs run in, information is power, so no secret is safe.
Verdict: Upper East Side. It may be tougher, but at least you don't have to deal with Miss Patty and Taylor Doose all the time.

Your take? Are there a lot of similarities or have I become a conspiracy theorist after reading that Amy Sherman Palladino was supposed to turn the Gossip Girl books into a movie (according to the always reliable wikipedia.). There's just got to be something to the fact that both shows can be abbreviated GG. Right?