Blair has had her life all planned since she was 12 and now, at the tender age of 18, it’s in shambles. Of course, when one uses a Machiavellian philosophy in plotting one’s course in life, one needs a solid backup plan because the likelihood of being bitten in the ass is very high.
Blair has lost Yale, lost her dream, lost her way and seemingly lost her mind. She’s not returning phone calls from Serena or Chuck and is exhibiting wayward morals by drinking scotch before noon and sleeping with guys with pretentious names like Carter Baizen.
Chuck visits Blair one morning to discover that she and Carter have been spending intimate quality time together. Nothing matters anymore to Blair and she is bent on becoming everything that the old Blair was not — like horribly unpredictable.
Dan and Vanessa plan to hang out with Nate and watch some college basketball, but they meet Nate’s cousin, Trip, upon their arrival. Trip (wonder if his brother’s name is Stumble) is encouraging Nate to visit the Vanderbilt family compound for a family reunion. Nate’s maternal grandfather will be there and, for Nate, that’s the deterrent. He feels that his grandfather left him high and dry when Nate’s family was struggling due to his loser dad’s embezzling ways. Dan and Vanessa convince Nate to go because he has always loved and respected his grandfather.
Lily continues the art renovations of her home. She’s working with an art buyer who, at one point, dated Rufus. When the woman brings up what she believes is the elephant in the room (that she dated Rufus), Lily acts as though she knew this all along. She didn’t. Lily confronts Rufus later for not giving her a heads-up to how he knew this woman, and that leads to Rufus and Lily pledging to come clean with each other by making a list of all of those fortunate souls whose hearts and other parts they have touched in that biblical way. A sex-with list written by a quasi-rock star and a rich groupie? They must still be getting high because that’s an atrocious idea.
Nate heads out to the Vanderbilt home with Dan and Vanessa in tow. They watch as Grandfather helicopters in. Yeah, that kind of rich. Grandfather is excited to see Nate and the chill is immediately thawed. Grandfather even says he was proud of how Nate handled the situation of his parents’ shrinking financial resources. Grandfather was apparently unaware of Nate being a ho with The Duchess but I won’t tell, if Nate doesn’t tell.
While all the virile young men in attendance play an overly spirited game of touch football, cousin Trip’s fiancé gets in Vanessa’s ear about how Grandfather is one persuasive guy. He usually persuades the young men to pursue positions in politics or law. No silly bohemian majors for a Vanderbilt legacy! Does that mean Nate’s Lesbian Studies major is in jeopardy? Oh no!
Serena and Blair meet up to go shopping or, well, Serena goes shopping and Blair goes shoplifting as she steals a pair of sunglasses from a store that probably marked the glasses up 500 percent over cost anyway, but that’s not the point. Blair tells Serena that being Blair has been really tiring. Being perfect and planning and plotting really takes a toll on a person, and now that Yale has been yanked from her, why bother maintaining that level of anxiety. Serena tells her that it’s not like Blair to just give up and that she needs to keep trying to persevere. Serena loves her friend and is worried. So sweet.
Chuck has tried to dig up dirt on Carter to blackmail Carter into leaving town and leaving Blair alone. Turns out Serena is the one with the dirt, and they invite Carter over to hang a dirt bomb over his head and it works! All Serena mentions is what she knows about Carter on the island of Santorini. Carter says that Serena was involved too but agrees that leaving town rather than have Serena talk to authorities was the better choice. Good grief. What, has Serena killed another guy? She’s a serial killer now?
While at Serena and Chuck’s, Carter mentions that he and Blair were going to attend a party later, and Chuck assumes it’s one of those secret society-type parties. Chuck and Serena browbeat Dorota for details as to Blair’s whereabouts. Dorota gets so annoyed by their harassment she drops the smack on them in Polish! When they make her understand their genuine concern, Dorota gives up the address to where Blair was heading. They rush over to the address expecting to find a den of debauchery but instead stumble upon Blair begging and pleading with the admissions dean of Sarah Lawrence to please let her apply. A groveling Blair was hard to see.
Rufus and Lily have dinner and it’s time to play show me yours and I’ll show you mine with their sex-with lists. Lily was given advice from Serena earlier that she better see Rufus’ list first before whipping out her multiple pages of names. Sure enough, Rufus had a decent list of 12, but come on, Serena’s list is probably longer. Lily, out of shame, only pulls out one page of hers and they call it a night. Needless to say, Rufus finds page two later and feels that he can’t trust Lily. I guess the pregnancy and baby adoption wasn’t enough of a hint.
Vanessa expresses her concern to Nate about him falling victim to family expectations. She worries that Nate will not follow his heart but will do the safe thing. Nate vows that he will not change. Of course, this means he’s going to change at the first available opportunity.
Nate, encouraged by Vanessa, agrees to meet with cousin Trip and Grandfather for an evening with the guys. Unbeknownst to Vanessa, Grandfather set up Nate with an internship in the mayor’s office for the summer. That would be cool except Nate and Vanessa had previous plans of backpacking and roughing it through Europe over the summer.
At the Vanderbilt luncheon the next day, Blair, who’s a tad tipsy, puts many of the stodgy old guests on full blast about their own secrets and transgressions. Serena and Chuck follow her around the gathering trying to do damage control.
Chuck finally corners Blair, and she asks Chuck to take her right, then and he mumbles something like she’s not being the Blair he wants and blows yet another opportunity with the girl. That’s the third strike, fool. You’re out!
Blair finds a quiet spot to do some soul searching and Nate wanders in looking for his soul as well. He was just confronted by Vanessa over the possible summer internship offer. In a very sweet moment, Nate and Blair stroll down memory lane back to when they were 12 and 13, and how different things have turned out now. Nate acknowledges that he always felt burdened by his wealth and privilege but has come to the conclusion that his family is his family and trying to deny that is what had him lost all these years.
Nate goes back inside and publicly accepts the internship offer, hurting Vanessa in the process.
After telling Lily that he can’t trust her, and after Lily tells Rufus that he’s ashamed of her past, Rufus comes back over to ask for a list of all the things that make Lily happy. He wants to make byegones remain gone. Well, until their spinoff hits the air.
Back at the their own house, Chuck worries to Serena that he’s losing Blair, and Serena tells him to fight for her and that he knows exactly what he needs to do and say. When Chuck gets to Blair’s, Dorota tells him that she’s asleep and that he should come back tomorrow.
Chuck glances over and sees the jacket that Nate wore at the luncheon and knows Nate’s there. Upstairs, Nate is preparing to leave when Blair takes his hand and asks him to stay.
Wow. So, Blair’s back with Nate? Who saw this coming? Chuck won’t take this turn of events without a fight, right? How long will Serena remain a peripheral character?