Chuck In Real Life is the 7th episode of the second season and the 25th overall.
There's nothing quite like autumn in New York. But it's not only the leaves that change. Something in the air brings out the true colors in everyone.
Vanessa blackmails Blair into helping her with a cause, which leads to Blair seeking revenge along with Chuck. Meanwhile, Lily and Bart throw an extravagant housewarming party but a rebellious Serena is not ready to play by their rules. Also, Dan and Jenny discover a big secret Nate has been keeping from his friends.
At the VDW's, Serena comes to the breakfast table to find Lily, Chuck, and Eric sitting silently. Bart also comes down and explains that his meetings wrapped up sooner than expected and he's back for the long haul. Lily mentions their housewarming party planned for the next evening and tells Eric that they're allowed to bring friends when he asks. She then asks Serena if she saw the suit Bart bought for her, and she says yes but she figured it was for the housekeeper. Bart announces that he and Lily have some new guidelines they thought up together; including weekly family diners, no more going out on school nights, and a weekend curfew of one AM. Serena demands to know whose idea this is, and Lily assures her that she and Bart made the decision together. At the Humphrey loft, Dan sees Vanessa gathering her fliers to save a bar in Brooklyn by petitioning for landmark status. Jenny jumps in and says that her parents and Eleanor already signed. Vanessa suggests she accompany Dan to school to see if anyone would be interested in signing. She then notices Dan carrying a sports bag and asks whose bag it is. He explains that Nate asked him to fill in on the soccer team because most of the team got mono. Meanwhile, Serena and Eric walk to school as she vents about the new rules. Eric tries to assure her that Bart isn't trying to control everything and Serena agrees to give Lily's new marriage and rules a chance.
At Constance/St. Jude's, Nate tells Dan that the coach was impressed with his try out. As they walk, they run into Chuck; who tries to get Nate to be his friend again. However, Nate blows him off and walks away with Dan. Immediately after, Blair approaches Chuck and mocks him for losing his best friend to Dan. Chuck reminds her of the time they slept together and asks when it will happen again. She assures him that that will never happen again and goes outside to lecture a girl about wearing tights as pants. As she does so, Vanessa asks for a moment of her time. Blair grants her request and Vanessa explains her campaign to save the bar before telling her that she has to obtain a thousand signatures or else she will tell everyone about Catherine and Marcus. She leaves Blair with the petition and leaves. That night, Chuck sees Serena in bed reading a book. He tells her that he's going out and that the new rules don't apply to him since he knows Bart only came home early to court some executives who won't do business with people with no family values. Chuck reminds her that unlike her, his business isn't spread all over Page Six and leaves. Serena thinks this over and gets ready to go out in a skimpy dress. She runs into Bart on her way to the elevator and announces that she's going to find some paparazzi. At the Waldorf's, Chuck arrives to see Blair; who presents him with a proposition. She tells him that Vanessa is bothering her and since Dan stole his best friend, he might as well steal his. She suggests he seduce and destroy Vanessa, then hands him a flier for the bar campaign. He agrees to her plan and they toast to it.
The next day, Blair and Serena have brunch together while they wait for Eric to bring his new boyfriend, Jonathan, so they can meet before the party. They talk and Blair mentions Chuck, and Serena notices her smiling a little when she says his name. At the loft, Dan explains his soccer practice to Jenny. She notes that maybe now he'll have guy friends. Confused, Dan asks what she means and she explains that Dan likes to hang out with girls more than guys. Rufus doesn't disagree and to prove them wrong, Dan calls Nate to see if he wants to hang out. Nate agrees and they make plans to meet that afternoon and play soccer. Meanwhile, Vanessa's friend and owner of the bar, Horace Rogers, is impressed at the turnout. Chuck arrives then and brings Vanessa one of her fliers. She refuses to hear out his plan and accuses him of wanting to turn the bar into a yuppie fashion bar. He says that he would restore the place to it's former glory but she says she knows him. He asks if she really does or only thinks she does before he gets hit with a slushy. He gets back into his limo and leaves. At the VDW's, Serena arrives home and is confronted by Lily for her antics the night before. Lily says that Serena could benefit from a little structure and Serena retorts that she should have pushed for that several husbands ago. Hurt, Lily says that was unkind to say and Serena says she isn't coming to the family party that night. Meanwhile, Dan arrives at Nate's house and finds a bunch of notices from the state establishing the home as seized and under federal investigation. However, he finds a way into the house and discovers that it's completely empty except for a sleeping bag and several garment bags of dry cleaning.
At the Waldorf's, Chuck arrives to see Blair and tells her that their deal is off. She begs him to reconsider but he says that it isn't worth the effort if the payout isn't worth it. She offers to make it worth it and alludes to letting him have sex with her if she succeeds. Chuck mulls it over and decides to try again at succeeding. At the VDW's, Vanessa comes to see Chuck. She says that his lawyer brought by his official proposal, which did indeed include keeping the bar as is and petitioning for landmark status. He asks why she came to the apartment and she says Horace wants to officially meet him to feel comfortable with signing his support over. He agrees to go get dressed. Meanwhile, Serena goes to the Waldorf's and vents her complaints to Blair as she gets dressed for the party. They reminisce about Lily's many boyfriends and husbands and the toll it took on Serena and Eric. Serena compliments how gorgeous Blair looks and asks where she got her dress. Blair admits that Chuck gave it to her when they were supposed to go to Europe. At the park, Nate and Dan have wrapped their soccer game and Nate asks if Dan is going to the housewarming party. Dan says no, and Nate says he isn't going to go either. He also says that he would invite Dan over but the house is a mess since the housekeeper has the week off. Dan asks where his mother is, and Nate says she is still in the Hamptons and thinks he's staying with Chuck. He excuses himself to get a drink. At the bar, Chuck is impressed and meets Horace, who compliments him and welcomes him warmly.
At the loft, Jenny gets a call from Dan, who explains to her what he saw. She explains that Nate is probably embarrassed to admit his situation. She suggests he invite Nate for dinner to have Rufus' chili and then they can convince him to stay. Dan agrees and asks her not to say anything to Rufus. They hang up and he extends the invitation to Nate, who accepts. At the VDW's, Serena arrives home to find Jonathan in the living room. She asks if he's there for Eric and he explains that Eric isn't home, he was just dropping off some books. Confused, she asks if that means he's not coming to the party and Jonathan explains that Bart told Eric the party was family only. Back at the bar, Vanessa asks Chuck if he's serious about saving the place. He says yes, and she apologizes for misjudging him. As he's about to say something else, he gets a text from Blair, who is wondering how it's going. He ignores it and invites Vanessa to come to the housewarming party.
At the party, Lily notices Serena and Bart goes to handle it. He compliments how the suit looks on her and says they're glad she came to the party after all. She says she's waiting on some friends, then asks if it's okay for friends to come. He says yes and she asks him if Lily knows he told Eric he couldn't bring Jonathan. Bart explains that he didn't tell Eric that, and that they had a talk which led to Eric coming to the decision all on his own. Meanwhile, Blair approaches Chuck and asks for a progress report on the plan. He tells her that he is going to really buy it, and she tries to ask him if he's still going to humiliate Vanessa. He distractedly says yes and excuses himself to greet Vanessa, who just arrived. Blair notices the two together and Bart asks for a moment to speak with Chuck alone. At the loft, Dan, Jenny, Nate, and Rufus finish dinner. Rufus asks Nate how his home life is, and Nate admits that he's staying alone while his mom is away but that he's fine with it because it's his childhood home. Back at the party, Bart confronts Chuck about buying a bar behind his back. Chuck says it wasn't supposed to be a secret and that it's a great business deal for all involved. Bart accuses him of betraying his trust and wasting his time. Back at the loft, Nate helps clean up and then tells Dan that he should probably go home. Before he leaves, Dan admits that he saw his living situation and that he wants to help. Angry, Nate tells Dan that just because they've hung out a couple times doesn't mean he needs to involve himself in the situation. He orders him to stay out of it and leaves.
Back at the party, Vanessa finds Chuck sitting alone in Serena's room and says she overheard his conversation with Bart. She says she's sorry and that he deserves a better dad. He replies that she still doesn't really know him and Bart made some good points about him. She goes to leave but Chuck takes her hand and asks her to stay. Blair walks in on this and is hurt by what she sees. In the main room, Eric tells Serena that Bart told him he could bring Jonathan but that he should be sure that he wants to come out as gay in front of all the press that will be at the party. Serena says he is only worried about his deal, but Eric admits that he really doesn't think so. While they talk, a couple reporters come up and ask for a quick interview. Lily notices this and asks to borrow Serena before she says something wrong. Lily offers to talk about a family trip to Mystique that they took but Serena takes the opportunity to mention that Lily put her boyfriends before her own kids, even the ones that do drugs. She then tells Lily that she was wrong to accuse Bart of being controlling and out of place, and that it's really been her doing all along. Meanwhile, Blair tells Chuck that their deal is off because she's bored with the game. She explains that Vanessa isn't worth either of their time since she's so beneath the both of them. Chuck suspects that she's worried he'll succeed and she assures him that it's not that. He asks what it is then and she hesitates before telling him to forget it. Elsewhere, Lily vents about what Serena did to Eric. She asks him if what Serena said is true, and Eric says that while her timing was bad, she was absolutely right. Eric finishes by saying that they need to become a family by bonding and not just by telling everyone they are.
At the loft, Dan and Rufus sit together and Rufus notices Dan is still upset about what happened. Dan says he tried to help Nate and it's not his fault that he bailed. Rufus says that being a friend includes giving someone what they need even when they don't ask for it, and that it also includes offering help even when it's turned down. Dan refuses to do that, and Rufus replies that his situation is intense and that Nate really has no one looking out for him; and that Dan has the opportunity to do so as his friend. Back at the party, Vanessa is having trouble locating her bag at coat check. Blair then appears and announces that she took her bag to get her cell phone; and she deleted all photos of Catherine and Marcus. She also explains that Vanessa did not find the "hidden" Chuck, and that any feelings she thinks he might have for her were all a part of a bet they had to humiliate her. Vanessa says she doesn't believe her and that Blair is probably just worried that Chuck is a decent person when he isn't around her. Chuck comes over then and asks Blair what she's doing. She answers that she was just explaining their game to Vanessa to make sure she understands that she was just a chess piece that needed to be knocked over in order for Chuck to take the queen. She asks if he disagrees and he says nothing. Hurt, Vanessa says she should have known and leaves. Chuck then asks what the point of that was and Blair says she was humiliated like she wanted and he won the game; his prize will be in her bedroom in one hour.
Meanwhile, Serena runs into Dan on the street outside Nate's house. She asks him to sit with her. At the bar, Chuck goes to see Horace; who already heard from Vanessa that the deal is over. He tells him to leave, and Chuck says he is still going to try to save the bar. Horace replies that he was dead wrong about Chuck and offended, he leaves. Back at Nate's, Dan tells Serena that he came to see Nate as a friend and she says she came because she needed to get out of her house. He asks her to pretend he's Nate so she can talk openly. She explains about the party and what she did to Lily in front of everyone. Dan suggests that maybe Lily tries to act like she's perfect because she can't acknowledge how far from perfect she really is. She apologizes for everything that happened with them and he does too. Immediately after, Bart pulls up and asks to take Serena home. She tells Dan that she should go home and test his theories; then says she's glad he's Nate's friend because he really needs a friend like Dan. Back at the VDW's, Serena and Bart find the apartment empty except Lily and Eric. Lily apologizes to Serena for not being a good mother for the first seventeen years of her life and they all reminisce on funny stories from years past. Serena apologizes for the magazine snafu and then apologizes to Bart for how she acted before. He accepts her apology and they all eat cake together as they make up. At the loft, Dan brings Nate home and Rufus and Jenny welcome him by telling him to make himself at home. At the Waldorf's, Chuck enters Blair's room to find it filled with candles and her on her bed in lingerie. She asks what took him so long and they begin to make out. Before they do anything, he asks her to say the three words she asked him to say. She refuses and says she will never say those words to him. He responds by getting up and saying she will never have him them. Shocked, she asks if it's because of Vanessa and if it is, he needs to remember that it was just a game. He answers that he wants to raise the stakes and that it's now time Blair chased him, as he's been chasing her for too long. He then leaves Blair alone in her room as he goes home.
- 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
- Kelly Rutherford as Lily van der Woodsen
- Matthew Settle as Rufus Humphrey
- Connor Paolo as Eric van der Woodsen
- Amanda Setton as Penelope Shafai
- Robert John Burke as Bart Bass
- Nicole Fiscella as Isabel Coates
- Matt Doyle as Jonathan Whitney
- Chuck Cooper as Horace Rogers
- Honor Brodie as Herself
- Take Back the City by Snow Patrol
- One Week of Danger (Demo Version) by The Virgins
- Snowflakes by White Apple Tree
- Psychotic Girl by The Black Keys
- Sea Out (Solo Piano Version) by Guillemots
- Hard Times by Mildred Anderson
Bart: As tomorrow evening marks our debut as a family, we've been talking about what that actually means.
Chuck: Less money for me when you die?
Chuck (to Blair): We're inevitable, Waldorf.
Penelope: Kelsey, Kelsey, Kelsey. How many times must we tell you, as one of the girls of the steps, you represent Constance royalty.
Isabel: So it should come as no surprise that many girls before you have gotten the axe when their choices reflected poorly on us.
Kelsey: I didn't realize-
Blair: THAT TIGHTS ARE NOT PANTS? Honestly.
Blair: Charity is for diseases and endangered species. Real estate is not on the list at least not in New York!
Dan: Dad, will you please tell Jenny that I have guy friends?
Rufus: Sure he does, I'm his-
Jenny: Not including you.
Rufus: Uh, Cedric?
Jenny: Not including dolls.
Jenny (on Dan's plans to hang with Nate): Is Cedric invited?
Rufus: Jenny, come on.
Dan: Thank you, Dad.
Rufus: You know Cedric would get dirty... then Dan would have to bathe him.
Chuck (to Vanessa): Did you have a reason for coming here? Because if it was to insult me there's a website you can go to.
Blair: What took you so long?
Chuck: If you thought that was long, you have no idea what you're in for.
Chuck: Say it.
Blair: Say what, I'll say anything.
Chuck: Say those three words you wanted me to say.
Blair: Are you kidding?
Chuck: Not quite. Eight letters, three syllables, say it and I'm yours.
Blair: But I'm already yours and you're ruining the mood with all this talk-
Chuck: You can't say it. You wanted it from me.
Blair: I'm prepared to settle.
Chuck: Maybe I'm not.
Blair: Chuck Bass, I... will never say those words to you.
Chuck: Then you will never have me.
Blair: Is this because of Vanessa? It was a game, Chuck. That's it.
Chuck: Maybe I'm prepared to raise the stakes. Are you ready to play that game? I chased you for long enough. It's time you chased me.
- The episode title is based off the movie Dan in Real Life.
- This is Jonathan Whitney's first appearance in the series.
- The episode takes place on a Friday/Saturday.
- 1 Oak - Serena says she's going to this nightclub
- Bijoux - Serena says she's going to this lounge
- Brooks Brothers - Dan says Nate has a lot of these shirts made by this luxury brand
- Dutch Schultz - Dan mentions this famous criminal mobster
- Gibson - Dan says that he broke Rufus's guitar from this company
- Instyle - Lily introduces employees from this magazine to her guests
- J Sisters - Blair texts Chuck that she's on the way to this beauty salon, most likely getting a bikini wax
- Pain Quotidien - Vanessa mentions this french bakery
- Savile Row - Horace notices that Chuck's suit is from this luxury brand
- Scattergories - Dan tells Nate they will be playing this creative-thinking game
- Whole Foods - Blair says that Vanessa should be at this supermarket
- Ibizia - Blair mentions how Lily went to this island
- Mustique - Blair mentions how Lily went to this island