5 Dare Devil
Dan makes elaborate plans to impress Serena on their first official date. On the same night, Jenny is invited to the infamous Blair Waldorf sleepover and finds herself in a high-stakes game of Truth or Dare.
Truth or Dare at the Waldorf Soiree
Blair’s Annual Sleepover — the Waldorf Soiree (tradition since 2000). You’d think she’s holding a major convention — under her roof! Precision perfect placement of decoration, sleepwear, sleeping bags — No expense or reputation is spared.

Little Jenny Humphrey — REALLY? Going to her first Sleepover at the Waldorfs. Playing dressup, truth or dare, girls kissing girls… J’s DARE: Jail-break Eric van der Woodsen out of Ostroff! Blair diverts the attention of the nurse with a Code Yellow. They make the outbreak!
Jenny makes an outstanding play out of sneaking into and out of(!) the Eleanor Waldorf store. Blair had dared her to take a jacket off the mannequin, handing her own set of keys to the shop.
Dan and Serena’s Date
Dan breaks his Teenage Mutant Ninja Turtles piggy bank so he can splurge on his date (FINALLY!) with Serena. Dan picks her up at The Palace all snazzed up so jeans-and-shirt Serena has to change into something ‘less comfortable’.
Dan kind of makes a fool of himself at fine dining with Serena. Luckily, the night is saved with a pool game in a bar with a jukebox. There has to be the cheesy how-to-hold-the-cue-stick lesson.
Trouble with the Humphreys
Rufus calls Alison in Hudson to tell her about her painting being sold to Lily — but a guy (Alexander) picks up her phone. Poor Rufus.

When Eric broke out, Lily came over to Rufus’ in Brooklyn to ask for his help in finding Eric. Lily and Rufus make a home-cooked dinner.
Lily picks up the Humphreys’ phone… and it’s Alison calling! What a nightmare.
Memorable Lines
Jenny to Dan: I know who Blair and those girls are. But I know who I am. And I’m not gonna forget that just because I hang out with them.
Dan to Rufus: How long can a man have a piggy bank… and still call himself a man?
Blair to Jenny: And your face looks like it’s going to Bat Mitvzah
Blair to the Nurse at Ostroff (looking wasted): OK! I have a big problem. Caffeine, nicotine, ketamine, GHB, LSD, PCP… pam, all the pams really. I don’t discriminate.
Tribeca Star Comments
It was pretty unbelievable how Jenny got out of that mess with the police rushing to the Eleanor Waldorf boutique. That took a lot of gall and quick-thinking. Why does Jenny have to look so smug when she came back to the Waldorf’s Penthouse with the jacket. Actually she pretty much acts like that most of the time. It’s unreal.
The revised Dan Humphrey date was kind of cheesy with the pool lesson and jukebox in a bar. But oh so typical… reminded me of my cheesy flirting tactics in the old days. Lily makes her moves far better than Serena — so effortlessly pretty.
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