Well, let’s see:

Dan first, because I hate him most of the three. It started in season 1, the way he treated Serena sometimes, and in season 2 I really started to dislike him.
Dan thinks he is morally superior to all the Upper Eastsiders, simply because he is “poor”. He is always quick to judge people when they do something he thinks is wrong, but at the same time, rarely aplogises for his own screw-ups. For example, he made Serena tell the director about the pool-party when there was barely anything at stake (never would they have explused the entire class) and had the nerve to be pissed-off when she wasn’t expulsed? I mean, I get the whole the-world-is-so-unfair blablabla but Serena was his girlfriend who he claimed to love, shouldn’t he have supported her? Or at least have been relieved that she wasn’t going to be sent back to boarding school???
That’s just one moment, but there were quite a few of these kinds of incidents where I just disliked his behaviour.
Also, he slept with a teacher, while his relationship had just ended/was still uneasy. Did he ever admit that was wrong? I seriously cannot remember. I actually started to like him a bit better in season 3, although he was quite a jerk to Vanessa as well, and then he punched Chuck for having consensual, drunk sex with Jenny-the-drugdealer, who he just one second ago fiercely condemned, but hey.

Rufus: I don’t really care about him all that much.

Jenny: I liked her fine in season 1 & 2, even though she was mean sometimes, but in season 3 I hated what was done with her, the whole drugdealing plot was horrible, I will never be able to root for someone to smuggle drugs successfully to an ambassadors daughter (what where the writers thinking?) and the whole stealing-Nate thing made me really hate her. It was horrible and extremely selfish of her. In the last episodes, I felt a bit sorry for her because she had really hit rock-bottom, but still, the whole Nate thing left a bad taste in my mouth.

I LOVE JENNY DON’T BE MEAN TO HER

Oh, god, where do I start? One character at at time, I suppose.

Dan — ugh. In season one, when he was with Serena, he was all right. But he always acts like he’s so much better than everybody, so much more moral, when he sinks to his own lows all the time. Like when he SLEPT WITH MS. CARR. Or when he tried to sabotage Blair when she was going to tell Chuck she loved him. THANK YOU, HUMPHREY. You basically got us half a season of Friends-esque ‘will they or won’t they’ and completely idiotic plotlines like the whole ‘gentlemen’s club’ bullshit. So, thank you, Dan. In season three, every single one of his arcs was completely awful, boring, and pointless. Not that I can say anything better about the other characters (-cough- Evelyn -cough-) but still. Liking Vanessa came completely out of nowhere and they were an atrocious couple. But I digress, because I don’t think it’s fair to judge a character’s worth on the trainwreck that was season three.

Rufus — somehow, he kills me the worst, because he is just SUCH an idiot. Season one–’OH HAI THAR LILY I DIDN’T SEE YOU I’M MAD AT YOU FOR SOMETHING THAT HAPPENED IN OUR VERY COMPLICATED PAST THAT IS NEVER FULLY DESCRIBED.’ I don’t even remember his plotline in season two, but in season three, he basically became a doormat, not realizing that his wife had CANCER (did she really have cancer? God, I don’t even know) and was seeing her ex-husband right under his nose, was blatantly trusting to the point of complete idiocy, and OH MY GOD DO YOU REMEMBER THE REAR WINDOW THING WITH DAN AND VANESSA WHERE HE WAS ALL ‘OH, VANESSA, I DIDN’T KNOW YOU MADE FLAN’ AND THEN HE JUST STOOD THERE AWKWARDLY UNTIL THEY /INVITED HIM IN ON THEIR DATE./ Plus, plaid shirts and waffles. Doesn’t this guy have a job?

Jenny — season one Jenny, I really didn’t mind. I didn’t love her, but I didn’t hate her, and I thought she brought a nice connection between Brooklyn and the UES, between the two different lifestyles. Season two, she was okay, and despite that brief thing with Nate that was incredibly gross, I thought the whole Agnes-fashion-half-naked pictures thing was actually a somewhat decent plotline. Then…I don’t remember what she did for the rest of the season, but anyway. Season three…oh, my. Oh my goodness. She became a completely insufferable character on all possible levels. She dressed like a combination between a street corner whore and a sea creature. She basically became a nasal bitch, trying to break up Nate and Serena, UNDERMINING HER OWN BROTHER’S RELATIONSHIP WITH ONE OF HER BEST FRIENDS, WHAT THE HELL, NATE IS NOT ALL THAT SPECIAL (okay, he’s gorgeous, but come on, get a grip.) And then sleeping with Chuck, which I guess wasn’t really her fault, but if you recall: she came to his apartment, he gave her the opportunity to leave, she didn’t take it. And Chuck is an ass, but that’s another point altogether. But it really just showed how low she sunk. She basically alienated everybody, her father, her brother, her stepsister and friend, except for Eric, whose awesome was too strong to be sucked away by the terrible writing of season three.

All I can say is, I’m glad she’s gone. With Vanessa in Haiti, the only thing that could make this more perfect is if Rufus, like, divorced Lily and moved to Tibet.

Well i think the main reason they dont fit in the upper eastside world and therefore they give everyone the chance to hate ‘em because they are different and with different i mean partly really annoying!
Sometimes this whole victim thing can be really boring and it’s always the same, actually they arent poor, i mean even the rent for their loft must be really expensive (we wont concern the private school) and Rufus can efford all this with is old rockstar money…but nevertheless every wannabe is a wannabe which is why they annoy me.
i wanna look gossip girl because of the gossip, high fashion and lifestyle and not because i am so in love with the humphreys, which i am not.