Whether it's alcohol or coke, Serena (Lively) and all the Gossip Girl characters have an affinity for any sort of substance that will give them a buzz. Though a lot of the crazy things Serena did were in her past, she definitely saw a few downfalls on the show, none of which would be a shining example for a child on how to behave when things don't go your way.
Now, don't get us wrong: We, as the target audience, can definitely appreciate any excuse to see Chace Crawford with less clothing, but that scene is almost too hot for TV, let alone a child's eyes. Mommy Lively should definitely fast-forward through that one.
The Season 5 finale really saw Serena, arguably, at her lowest. Not only does she have sex with Dan while he is in a relationship with Blair, but she records the whole thing! This leads to her leaving town, but not to recover. Instead, she goes for the drugs and more random hookups. Let's just agree Serena isn't the best role model.
The whole thing goes down at the end of Season 4. And while Lily definitely makes some mistakes, it's her mother! How dare she. Let's hope Lively's children won't be so easy to turn on her. Of course, Lily takes responsibility and confesses to the crime, saving Serena from the burden.
The whole ordeal comes to light during Season 1, where Serena's past returns to haunt her in the form of Georgina Sparks. Long, complicated story short, Serena blames herself for Pete's death because they both did cocaine at her suggestion to help them get in the mood. Though her guilt is eventually absolved when she does the right thing and talks to Pete's parents, that whole mess of a night is definitely not PG.
These girls are frenemies at their best. Blair thinks Serena is stealing her dreams of Yale and the two go at it during a university party — right in front of the Yale administration. It's a designer catfight complete with the line, "Ow, my headband!" Let's hope Lively's baby doesn't ruin any college aspirations or designer headbands in a similar fashion.
This one, admittedly, doesn't involve Serena, but it was arguably the most OMG moment on the show. Lizzie McGuire (aka Hilary Duff) is all grown up and is definitely not a Disney darling anymore when she appears on Gossip Girl as Olivia and begins dating Dan. Add Vanessa in to the already hot and heavy relationship and you get an awkward morning.
Dan's dad and Lily's mom get married, which means Serena and Dan face a little bit of a family love affair. Granted, their relationship blossomed before the marriage, but there's no going back after their parents say "I do."
This may be Serena's most dysfunctional relationship — and that's saying something. Luckily, instead of agreeing to be Tripp's long-term mistress, Serena opts out of the relationship. Hopefully, Lively's child has the good sense to not go there with a married man to begin with.
It is revealed that Lily posed nude and, instead of being horrified, Serena thinks it's pretty sweet. "You are, like, the coolest mom ever!" is the quote. We're all for being comfortable in your own skin, but this instance just takes it one step too far.
She does this so Serena will participate in the debutante ball, because if your grandma is dying, of course you take the opportunity to show off to the other socialites. We just hope Lively's little one isn't so concerned with making a show of things.
Nate's teenage girlfriend, Sage, needs to stay in school, so it's Serena to the rescue, although she was pretty ineffectual. Serena isn't exactly the poster child for good examples when it comes to staying in school and staying away from drugs.
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