Serena and Nate: Their steamy hookup has been captured on the OMFG ad campaign, but really took place before Serena left NYC and returned. Though Blair forgave Serena for hooking up with her BF, is Nate really over S
2 of 11 Patrick Harbron/The CW
Dan and Serena: When Serena returned to NYC with her reputation in tatters, she had no idea she could find happiness with a "nice guy" like Dan. But, how long can any couple remain happy in high school--especially this high school.
3 of 11 Eric Liebowitz/The CW
Nate and Jenny: Nate thought that this lovely masked lass was Serena and planted a wet one on her. But alas, it was Jenny! Even though it was a mistake and they are "just friends," something tells us this isn't the only Nate/Jenny hookup we'll see.
4 of 11 Giovanni Rufino/The CW
Nate and Vanessa: Who knew that Dan's ex from way- back-when would end up hooking up with Blair's damaged goods I guess in a group this small, there's bound to be some... er... overlap.
5 of 11 Eric Leibowitz/The CW
Chuck and Blair: Mirror, mirror on the wall, who's the most scandalous hookup of them all Chuck and Blair, of course. She lost her virginity, not to her boyfriend Nate, but to Chuck... and in the back of a limo no less.
6 of 11 courtesy The CW
Chuck and Jenny: Oh Chuck. He manipulates, lies and charms women into doing whatever he wants... except Jenny, here. Chuck tried to date-rape Jenny but was saved by her bro and Serena. Karma's a bitch, so watch out, Chuckie boy.
7 of 11 KC Bailey/The CW
Nate and Blair: When we first met our favorite GG Upper East Siders, Blair and Nate were the perfect happy couple... until Serena and Chuck entered the picture. That's what you get for having a snake of a best friend, Nate.
8 of 11 Patrick Harbron/The CW
Jenny and Asher: Though these two have only just begun to date, something tells us that Asher may not be the perfect guy for Jenny after all. There's something to be said for "too good to be true."
9 of 11 Eric Liebowitz/The CW
Rufus and Lily: This handsome pair were hot and heavy before their kids were born, but now Lily is engaged to Chuck's dad. However, these two can't keep their eyes off each other whenever they're in the same room.
10 of 11 Giovanni Rufino/The CW
Bart and Lily: Once again, Lily is choosing money and safety over passion and love by marrying Chuck's dad, Bart (and making S and Chuck siblings!). But can she go through with it Will Rufus let her
11 of 11 Eric Leibowitz/The CW
Harold Waldorf and his Italian Stallion, Roman: Maybe Blair's such a pain because her daddy ran off with a man to Italy. Talk about hot gossip! But, all is well now between dad and daughter, so why isn't Blair nicer yet Eh, that wouldn't be any fun.