While You Weren't Sleeping is the 16th episode of the fourth season and the 81st overall.
Mick, Keith, and their questionably costumed cohorts said you can't always get what you want. But that doesn't mean it's okay for anybody else to have it either.
Eric's 18th birthday arrives, along with a drama filled celebration when Damien blackmails him with the information he knows about the affidavit Lily forged against Ben. An impatient Blair decides to speed up the time table to jump start her career: but ultimately stretches herself too thin. Meanwhile, Serena is forced to choose between her family and a potential romance with Ben. Chuck and Lily reconcile and team up in order to save Bass Industries from Russell Thorpe. Also, Vanessa returns to apologize to Dan.
The episode begins with a fully dressed Dan about to leave the loft when he sees Ben and Serena hanging out on the couch. They explain they were up late playing Scrabble, and Dan says he's headed uptown for a meeting and leaves. After he's gone, Serena tells Ben she's headed to Lily's to help her plan Eric's birthday party. She asks him to come to the party, but he declines to avoid pretending things are okay with Lily. They agree to hang when she's done. At the VDW's, Eric is sick with the flu. Lily is leaving to go to a meeting, and Rufus reminds her to stay strong. At the Waldorf's, Dorota is dressing Blair while she talks to Serena. She asks if her sudden addiction to work has to do with Chuck and Raina, but Blair denies it and asks her to explain where she was the night before. Serena admits she was with Ben, but that nothing happened. While Dorota is brushing her hair, Blair reads on Gossip Girl that Raina is the new face of Girls, Inc. and that Chuck is interested in getting her back. Disheartened that Raina has a powerful position at a company, a foundation, and Chuck, Blair decides to move up her timeline.
At The Empire, Chuck reexplains what Russell did to Nate. He asks Nate to "bump into" Raina and keep her occupied until he can return and convince her to give him another chance. Nate is hesitant, but agrees. At W, Blair meets with Penelope, Jessica, and a new minion, Emily, via Skype. She instructs Penelope to buy a housewarming gift for Eleanor and a birthday gift for Eric, Jessica to attend her Art History exam and write her essay via bluetooth dictation, and Emily to get her a meeting with Bryn Harold to get on the board for the opera. After they hang up, she begins to dictate tasks to her interns but instead learns that all of them put in for transfers. However, Dan shows up and Blair announces he is her new intern. Meanwhile, Chuck meets with Lily at The Oak Room but she tells him to stop calling, despite his trying to apologize. He tries to blame Russell, but she defends him. He accuses her of cheating on Bart and Rufus, and she slaps him before leaving. Chuck pays his tab and leaves, and it's revealed Russell was also at the bar and heard the whole conversation. At the VDW's, Serena waits in the lobby for Ben, and when he arrives, she tells him that the party was cancelled so they can hang as soon as she wishes Eric happy birthday. Ben notices Eric in the background, and points him out to her. She asks what he's doing, and he confesses that he isn't sick. Elsewhere, Chuck gets into his limo; where Lily is waiting for him. It's revealed they staged the fight in front of Russell in order to save the company.
Back at the VDW's, Eric explains that Damien is blackmailing him with the information about Lily, and is forcing him to pick up a flower shipment containing coke inside the plant food packets. Serena promises to find a way out of it for him, and tells him to tell Lily not to cancel the party. He heads back upstairs, and she tells Ben she's going to get the drugs herself. He warns her not to, and encourages her to let Lily take the fall and pay for what she did. However, Serena refuses and leaves. At W, Dan refuses to work for Blair, but quickly sees that she's in over her head with work. He offers to help as a friend, but only as a friend, not a servant. Meanwhile, Nate catches Raina outside Bergdorf's. She notices her car is gone, and plans to take a cab to her next meeting but Nate convinces her to walk through Central Park with him to get there. At the VDW's, Lily is finishing planning the party while she waits with Chuck for Russell to call. They plan to have Chuck break into Russell's office while Lily is distracting him, and find the investor who is backing the purchase in order to tell him about how the company is more profitable kept whole. At that moment, Russell calls to invite Lily out for a drink; which she immediately agrees to. At W, Blair is still refusing to let Dan help her. As he watches, she is forced to take on several new tasks in addition to the ones she is already behind on. Serena and Eric arrive to ask for her help on a scheme, and she agrees to help as Dan leaves. Meanwhile, in the park, Nate convinces Raina to try ice skating since she has never been. Back at W, Blair calls Penelope and tells her to come by the office and take the purple sticky note on her computer with details for the flower deal. Dan then arrives back in the office and Blair admits she needs his help. She goes off to help Donna with a crisis, and tells Dan start with anything on the desk. He sees the purple sticky note marked "Urgent" and decides to start with that.
At The Empire, Raina excitedly tells Nate that she was happy to cancel her day and continue trying things she's never done. He tries to talk Chuck up, but she ignores him. Meanwhile, Lily and Russell meet while Chuck enters his office. While they talk, he logs into the system and is able to track down the investor. Lily lies to Russell that she and Rufus are having problems, and that she's planning to leave him after he buys Bass Industries. After Lily hears that Chuck got the info, she tells Russell she's leaving to go to Eric's party and they part ways. At W, Emily informs Blair that Bryn Harold will be at Eric's party, and Penelope reports that she bought the gift. Blair demands to know why she didn't get the flowers, and Penelope panics that she didn't get it. Blair goes to look for the sticky note she left for her and once she realizes it's gone, she figures out that Dan took it. At the VDW's, Dan arrives with the flowers. On his way in, he gets a call from Ben informing him that a girl named Vanessa is at the loft to see him. Dan tells him to tell her that he'll be in touch when he's ready and hangs up. Serena asks why he brought the flowers, and she and Eric quickly realize he picked up the wrong ones.
At the party, Blair arrives and is confronted by Dan and Serena for setting Dan up. Blair replies that Dan must have misread the sticky note, but he shows her that he didn't. Eric then comes over and says that Damien is on his way over now to collect the $100,000 he claims to be owed. Serena realizes that Eric has more than that in his trust fund, and they set off to find it in the pile of gifts. Chuck then arrives and tells Lily and Rufus that Russell's backer is a guy named Bradley Kidd, who lives in Georgia. Lily asks if he would consider backing them instead, and Chuck replies that he invited him to the party to get him to either back them or cancel his deal with Russell. At The Empire, Nate and Raina continue their day of having fun into the night. Chuck calls and asks him to bring Raina to Eric's party, but changes his mind when he sees Russell arrive. Back at the VDW's, Eric and Serena are opening gifts but are having no luck in finding the checkbook. Blair comes in and realizes that he got Eleanor's gift, and his gift is on its way to her. While unwrapping, Serena gets a text from Ben asking her to come downstairs. On her way out, she runs into Damien. Downstairs, Ben tells her that he knows she sent Dan to get the drugs, but she explains that she's not ruining Lily's life and heads back upstairs to help Eric. Upstairs, Blair tries to talk to Bryn Harold and Lily is surprised when Russell shows up. Russell tries to flirt with Lily, but Rufus comes up and confronts them, asking Lily if she's cheating on him. She refuses to argue with him in public, and promises to call Russell later. He walks off, and she tells Rufus he's not bad at playing double agent. Meanwhile, Bryn Harold is unimpressed with Blair, and asks if she's seen Chuck because she wants an introduction to Raina. On his way out, Russell notices Bradley Kidd arrive and decides to stay after seeing Chuck introduce himself to him. In Serena's room, Eric writes the check for Damien but before he can leave, Lily catches them and asks what he's writing the check for. Outside, Russell guesses Chuck and Lily's plan, and Chuck announces to Bradley about how Russell's plans don't make financial sense. Bradley decides to stay, and tells Russell he hates being lied to and cheated. Unbeknownst to them, Damien witnesses the conversation. At the bar, Dan sees Vanessa arrive. She tries to apologize, but he doesn't forgive her. In Serena's room, Eric finishes telling Lily the whole story. For the first time, she admits she was wrong in forging Serena's signature. Upstairs, Dan finds Blair alone. He admits he was hanging around her to avoid Ben and Serena. Emily comes in to take the bowl, and says that Jessica confused history with art history and she got an F on her test. However, she says she enjoyed her blog and Blair realizes Dan wrote and posted it for her. Outside, Damien is leaving with his check when Ben stops him, and threatens to have him killed if he ever tells anyone about Lily. He reveals that he set Howard up to be beat, and can have worse done to Damien. He grudgingly hands back the check and leaves. However, Vanessa is catching a cab and hears the whole conversation.
After the party, Chuck calls Nate to bring Raina over. However, Nate says that Raina figured out what he was doing and left. After they hang up, it's revealed Nate lied to Chuck and is still with Raina, who tells him that she wants to be with him. At the VDW's, the family eats cake and discuss the night's events. While they eat, Ben shows up and returns the check, promising Damien won't bother them again. At the loft, Blair arrives to see Dan. She tells him she knows he wrote the blog, and explains that she was fired but also quit. She admits she wanted to succeed to return to Chuck before he fell for someone else, but she failed in all aspects. After she vents, they agree to order pizza and hang out. At Russell's office, Damien arrives and proposes to tell him some useful information if he pays him $100,000. At the Waldorf's, Ben and Serena finally consummate their relationship. While they kiss, a call from Vanessa come onto Serena's phone. At the loft, Dan and Blair watch a movie and fall asleep together.
- Blake Lively as Serena van der Woodsen
- Leighton Meester as Blair Waldorf
- Penn Badgley as Dan Humphrey
- Chace Crawford as Nate Archibald
- Ed Westwick as Chuck Bass
- Jessica Szohr as Vanessa Abrams
- Taylor Momsen as Jenny Humphrey (Credit only, as she does not appear in the episode)
- Kelly Rutherford as Lily van der Woodsen
- Matthew Settle as Rufus Humphrey
- Connor Paolo as Eric van der Woodsen
- Amanda Setton as Penelope Shafai
- Kevin Zegers as Damien Dalgaard
- Zuzanna Szadkowski as Dorota Kishlovsky
- Michael Boatman as Russell Thorpe
- Tika Sumpter as Raina Thorpe
- David Call as Ben Donovan
- Alice Callahan as Jessica Leitenberg
- Kevin Collins as Bradley Kidd
- Lisa Lynn Masters as Bryn Harold
- Sunshine (Cataracs Remix) by Rye Rye
- Wires by Matt & Kim
- TikTok by Ke$ha
- The Thanks I Get by Erik Hassle
- The Phoenix Alive (The Octans Edit) by Monarchy
- The Cut by Quitzow
Blair (on sleep): Great leaders only need three hours - mine just happen to be non-consecutive.
Chuck (on Nate helping with Raina): Your Archibald charm can get me the opening I need. Just change the sweater.
Nate: What's wrong with my sweater?
Blair: I wanted to tell you... that you were right... about that thing.
Dan: And now which thing is that?
Blair: I, Blair Waldorf, need Dan Humphrey's help.
Dan: As a friend and peer, not an underling.
Blair *mumbling*: As... my friend and peer, not my underling.
Raina: What would you be doing if I wasn't here?
Nate: Probably just studying.
Raina: What subjects?
Nate: ....Well, I might be playing a little Black Ops first, yeah.
Raina *pulls joint out of robe pocket*: Would you be doing this too?
Nate: It does make me a better soldier.
Nate (on Wii Dancing to Raina): One, this isn't even a real sport and two, gloat all you want, just please don't tell anyone I danced to TikTok.
Lily: Do you know how gauche it is to open gifts at a party, before dessert?
Eric: I was just so excited to have a new addition to my stock portfolio.
Damien (on Lily catching Eric): Seems you van der Woodsens and Humphreys have a lot to talk about. Think I'm gonna get a cocktail, maybe some mac 'n' cheese.
Dan: I'm not gonna chase after you, Vanessa.
Vanessa: And I wouldn't stop for you if you did.
Nate (to Chuck): You can get any girl in New York, not to mention Europe, Australia, and several parts of Asia.
- The episode title is based off the movie While You Were Sleeping.
- Nate's shoe size is revealed to be 11.
- Blair's ideas for Eleanor's present include a framed photo of herself.
- The actress Lisa Lynn Masters, who guest starred as Bryn Harold, committed suicide on November 18, 2016.