Serena spent a lot of her time in Gossip Girl being confusingly nice and mean at the exact same time. You never really knew where you stood with her, whether she was being the girl who would go out of her way to make romantic gestures to Dan, or she was devising plans to make him jealous.
Either way, at the center of so much attention, she was pretty much forced into living a life of shamelessness, dishing out brutality and boldness in equal measure through her actions. We’ve collected ten of her worst moments.
She Kept Kissing Teachers
Even though Dan Humphrey is certainly the worst in this regard (as he kissed his teacher, Rachel, and then tried to shame Serena for doing basically the same thing) but Serena has done it twice, and it is illegal after all.
Ben and Serena met before the first episode of the show when she was at boarding school and had a pretty intimate relationship which ended up getting him fired and imprisoned. She didn’t learn from her mistakes, and during the reveal of this piece of her past, she flirted with and dated Colin, her professor at the time.
She Filmed Her And Dan Having Sex
Serena made a few really, really poor decisions regarding both the love of her life and her best friend. One of the worst comes directly from the worst storyline Gossip Girl every provided us with: Dan and Blair’s relationship. Serena got Dan to sleep with her, filmed it, and was going to use it to make Blair jealous.
Also, it was in the same place that she slept with Nate (when he was with Blair). It ended up backfiring pretty massively, though, as it was played on a huge screen at a ball in front of everyone, and Serena’s mum saw at least some of it.
She Covered Up Her Own (Very Public) Past
We all knew what Serena got up to in her days before season 1, and then we all knew how these days pretty much continued, unaltered, as the show progressed. Serena was plagued by a very public lifestyle and a strange, stalker website publishing her every move. As such, everything she did was public domain.
For some reason, she decided to try to keep all of her actions from Cyrus’ son Aaron. It’s a bold move, especially because it would take him about three minutes to uncover the real Serena. Did she really think she would be able to keep a hold of her new fake personality for an indefinite amount of time?
She Pretty Much Killed Someone
We all know that Serena didn’t literally kill someone. The cliff-hanger we got all the way back in season 2 when she dramatically told Blair “I killed someone” was brilliant and goosebump-inducing, but it wasn’t exactly true.
Even so, despite being underaged at the time, Serena had been coerced into filming a sex tape by Georgina, and (on camera) offered a line of cocaine to Pete Fairman. Obviously it was his decision to take it, but his overdose wouldn’t have happened without her pressuring involvement…
She Forced Jenny Into Partying
While Serena was always quite nice to Jenny in comparison to Blair’s borderline-bullying and total life-ruining, she still made her fair share of rough decisions regarding Dan’s strange sister. She ended up throwing Jenny a party (which she forced her to go to) just so she could prove her own abilities to still host a great party.
It’s pretty terrible to use the birthday of a child to push your own agenda, but Serena also ended up realizing just how much her plan failed and moved away for a while. Rightly so.
She Was A Terrible Friend
This is quite a wide-ranging issue with Serena. She was simply the worst friend you could imagine to almost everyone she knew. She slept with two of Blair’s boyfriends, spent the time she wasn’t dating Dan trying to make him jealous, ruined various parties with her antics and would send off a life-ruining Gossip Girl blast if someone even slightly annoyed her. It made her an explosive person to be friends with and a ticking time bomb that each character had to tread carefully around at all times.
She Slept With Blair’s Boyfriend Before The Show Even Started
It’s shameless to cheat on anyone, really. It isn’t exactly a shocking revelation in the world of Gossip Girl, though, because pretty much everyone cheated on everyone, with everyone, at some point or another over the six-season run.
However, Serena gets things off to a really bad start by having slept with Nate (Blair’s boyfriend at the time) before the show even started. Nate is one of the only characters with truly good intentions throughout; we expected better from him but didn’t really expect much more from Serena.
She Tried To Ruin Blair’s Future
Serena and Blair are supposed to be best friends, though this is pretty questionable. They’re at each other’s throats pretty much non-stop throughout the entire show, coming up with a variety of ways to discredit the other in every single episode.
Deep down, though, they’re best friends and they care about each other. When Serena went out of her way to show Prince Louis’ (the worst character in the history of the earth, by the way) mother Gossip Girl and all of Blair’s misdeeds, she basically intended to crumble Blair’s perfectly planned future. She should have thought a little more about the consequences of these brutal actions.
She Lied About Being A Changed Person
Right at the start of Gossip Girl, Serena shows up and tells everyone that she is a changed person who is leaving behind her center of attention life as the ‘It Girl’ of the Upper East Side. She’s going to stop looking down on people or spending her life wandering between her fancy school and elite parties.
She does it for about a week, slumming it out with a guy from Manhattan. She gets bored of it all pretty quickly and resumes her previous life as a privileged girl spending her time with privileged people as she carries out the privileged obligations of her privileged life.
And, Let’s Be Honest, She Married Her Stalker
When Dan is revealed to have been Gossip Girl this whole time, you’d expect that every single person in the Upper East Side would despise him forever. He’d be banished further than Jenny, and there would be a fair few people who’d literally want him dead. And fair enough, too.
In the opening scene of the show, Dan (calling himself ‘Lonely Boy’) was effectively stalking Serena and went on to do the same throughout the rest of the show. By the time we’ve flashed forward five years, the two are married. You have to be pretty shameless to marry the guy that everyone knows stalked you (and them) for five years.
