Roman Holiday is the 11th episode of the first season and the 11th overall.
Hey Upper East Siders, it's Christmas in New York. And along with the season comes the Constance Billard/St. Jude's bazaar where the only thing bizarre are the donated items for sale.
When Blair's father, Harold, comes home for the holidays with an unexpected guest: his boyfriend, Roman, Blair finds it difficult to hide her disappointment and hatches a plan to get rid of Roman for good. Jenny and Vanessa help Serena plan the best Christmas surprise ever for Dan, who may have a surprise of his own in mind for Serena. Finally, Rufus refuses to remain the understanding husband any longer after Alison's former lover calls the house.
At Constance, Jenny sings in the choir at the Annual Holiday Bazaar while Dan and Serena mill around looking at the various objects for sale. They're surprised by Vanessa, who brings Dan's Christmas present early. He opens it to find a letter stating that his story 10.08.05 is being published in The New Yorker's Summer Fiction Issue featuring 20 under 20. Shocked, Dan realizes he's going to be published and thanks Vanessa profusely for sending his story in secretly. Meanwhile, Alison and Rufus arrive at the bazaar. They run right into Lily and Bart, and they introduce each other. Inside the school afterwards, Lily and Bart run into Blair; who remarks that she didn't know Bart was in town because she thought he was with Chuck. He explains that Chuck is holed up in a Bass resort in Monaco and Blair says that explains his silence and walks away. Once she's far enough away, she texts Chuck that she knows where he is. She's then surprised by Serena, who comments on the giant candy canes she's carrying. Blair tells her that she and Harold get them every year as tradition and his flight got in 27 minutes ago. Serena hurries her to the curb and helps her hail a cab as Blair explains that she's hoping to convince Harold to come back to New York for good. Serena asks for her help in finding the perfect present for Dan but Blair can't come up with any ideas. She gets into the cab as they agree to see each other the next night. Blair arrives home to find Harold already in the penthouse waiting for her. They hug and then Blair notices that Roman, Harold's boyfriend, is there too. He hugs her as well and Blair gives him a candy cane to him and Harold. At the loft, Rufus, Alison, and Jenny decorate while Dan opens Christmas cards. He finds one from someone named Alex, who writes for Alison to meet him on Christmas Eve. Dan realizes it's not a Christmas card and Rufus asks why he's writing to her. She promises that it's over and she has no idea why he's writing to her. He believes her and decides to let it go to not ruin the holiday.
The next day, Blair, Eleanor, Harold, and Roman walk to the skating rink in Central Park together. Blair asks Eleanor to distract Roman but she refuses, saying she needs to focus her time on her meeting with the CEO of Victoria's Secret. Roman overhears and Eleanor explains that she's designing a line of retro chic sleepwear for them and Blair suggests she tell him more about it. She takes the opportunity to walk with Harold and he asks if Nate is coming to the party that night. Blair says that he's in Connecticut with Anne but said he'd try to make it back in time. Harold tells her that he and Roman bought a chateau near Lyon, France and he excitedly tells her about how beautiful it is. Meanwhile, a man walks up to Eleanor and asks where the skating rink is, as he's taking his niece skating. Eleanor directs him and he thanks her. Roman says that he was flirting with her, but Eleanor doesn't buy it. They arrive at the rink and Roman decides to join Harold and Blair in skating, despite not knowing how. At the cafe Vanessa works at, Dan reviews past 20 under 20 issues and thanks her again for submitting him. As she goes back to work, Serena arrives and presents Dan with her gift: a very ornate watch. He tells her that while he likes the gift, he has never given such an elaborate present so he can't accept it. She asks if she overdid it and they agree to set a limit of $50 to spend on each other. As she's leaving, Vanessa offers to tell her Dan's favorite used bookshop but Serena declines. Elsewhere, Rufus keeps Alison's date with Alex for her and meets him. He orders him to stay away from Alison, especially because she told him to leave her alone; but Alex says that is definitely not what she told him a couple days ago. Realizing Alison spoke to him and lied about it, Rufus decides to stay. Back at the rink, Blair watches Roman and Harold skate together until she gets a text from Chuck, who asks how she faked her virginity for Nate. While she rereads the text, Harold tells her to catch Roman; who is about to skate without support for the first time. Blair opens her arms to welcomes him but once he gets within touching distance of her, she sticks her foot out and trips him. He goes flying before crashing down on the ice. Harold helps him up and they leave the rink.
At the Waldorf building, Blair and Eleanor get in the elevator to go up to the penthouse. Blair vents about how Harold went to the ER with Roman instead of going to tea at The Carlyle with her, and that she doesn't understand how Roman stole Harold from their family but comes off so innocent. Eleanor scoffs that Roman wasn't so always so innocent, as he was once infatuated with another model named Freddy, who was a horrible scoundrel. She advises Blair not to ever bring up Freddy to Harold, as it is a sore subject with him. At the loft, Rufus returns home and tells Alison that he went and saw Alex for her. She admits to talking with him because he felt she owed him an explanation and that she didn't tell Rufus because there was nothing to tell. They talk about how other people aren't the problem with their relationship and that they changed as people. Meanwhile, Jenny helps Dan search online for a gift for Serena. She remarks that he needs to find her an extra special gift to make up for her Christmas, since she's living in a hotel and can't even have a tree. At the Waldorf's, Blair leaves Chuck a voicemail to ask him not to tell anyone about what they did. As she hangs up, Serena comes into the room and Blair says she needs her to sign into her old profile on a modeling agency site. She is able to log in and Blair is able to find Freddy's contact information. Serena confesses that the stores are all closing and she has yet to find the perfect gift for Dan so she's really stressing. Blair gives her a few ideas before calling Freddy. Afterwards, Serena returns to Vanessa's work and asks for help. Vanessa agrees to help, saying that Dan isn't really into things so she gets that finding a gift would be hard. Serena mentions that the only thing he really wants is snow for Christmas and she says she can't give him that. Vanessa asks if she's sure and they go off together.
That night, the Waldorf Christmas Party is in full swing. Lily, who is at the party, receives a call from Rufus. She asks if there's something he wants to say, then asks why he's calling. He says he just wanted to wish her a happy holiday, and she replies that she and Bart are flying to Anguilla that night so she will. After they hang up, she chastises herself for lying like that. Meanwhile, the man who talked with Eleanor at the park enters. She asks what he's doing there and he explains that Roman tracked him down and invited him. Eleanor tells him to enjoy the party before confronting Roman, who has crutches after the skating incident, about inviting him. He shares that Jack owns a prominent hedge fund with offices in Barcelona and London, and that he thinks Eleanor is very attractive. She says that's still no excuse but he reminds her that she could use his romantic help, especially since they've been friends for so long. Eleanor coldly replies that friends don't steal other friends husbands and walks away. Elsewhere, Blair calls Nate's housekeeper to find out if he ever left Connecticut. She learns that he left a few hours ago so she assumes he's on his way there now. Upstairs, Blair discovers Serena, Eric, and Vanessa preparing Dan's gift; which includes lots of paper, cutting, glue, and a video. Blair tells Vanessa that she wants to help and asks her to help her find scissors. They go into her bathroom, where she informs her that she likes Dan a little too much and she's watching her. Vanessa leaves immediately afterwards and Blair goes back downstairs. Lily enters the room and says that once they're finished with their project, she's taking them out for dessert. Serena replies that she can't but she knows Lily is probably going to tell them that she's dating someone new. Lily doesn't deny it and reveals that she is dating Bart. Serena and Eric are shocked, as they don't like Bart. However, Lily promises that their relationship is casual, they aren't talking marriage yet, and she isn't asking their permission.
Elsewhere, Dan and Jenny work together to carry a Christmas tree to The Palace to leave in the VDW's suite. Jenny wonders what Rufus and Alison are giving each other for Christmas and Dan admits that he thinks there's a real possibility that they might split up. Jenny blames herself for bringing Alison back but Dan assures her that she did the right thing. Back at the Waldorf's, Eleanor talks with Jack until she sees Freddy enter the penthouse. She excuses herself and demands to know why Freddy is there. He says that Roman invited him but Roman hobbles over and denies doing so. Harold also approaches and is shocked that Roman would contact Freddy within a few days of being back in New York. However, Eleanor quickly figures out that Blair invited Freddy, not Roman, and offers him the featured model position in her spring catalogue if he tells the truth. He admits that Blair said she would buy him a cruise and renew his gym membership so long as he came and said Roman invited him. Eleanor tells him that he will be featured in her catalogue when hell freezes over before asking him to leave, which he does. Once he's gone, Harold says he's shocked Blair would do something like that to Roman; who has only been kind to her. Eleanor explains that Blair is lashing out at him, not Roman, since she was so disappointed that he didn't come alone. At The Palace, Dan and Jenny try to figure out a way to sneak the tree into the hotel but are interrupted by Lily's arrival. She realizes what they're trying to do and suggests that Bobby, the security guard at the service entrance, could probably be bought to let them take it up; and asks them to follow her. At the gallery, Serena excitedly tells Vanessa that she texted Dan and he replied that he's on his way. Vanessa goes to leave but Serena asks her to stay to see his reaction. However, Vanessa insists that she has to go but wishes tells her to enjoy her night. Back at the Waldorf's, Harold comes in to tells Blair goodbye before he and Roman go back to Paris. Blair admits that she was going to convince him to stay in New York but she is now scared that there's no room in his life for her anymore. Harold promises her that he will always have room for her no matter what, and shows her a DVD; which is part of her gift. They watch it together, and Blair sees it's filled with photos of his new chateau. He points out the photo of her room, which he had decorated in her taste. She also sees a cat, which Harold explains is named Cat, like in Breakfast at Tiffany's, her favorite movie. Finally, he invites her to spend the whole summer in France with them. At the gallery, Dan arrives to find a 3D simulation of snow. He says he loves it and gives Serena her gift, which is a copy of his story 10.08.05. She asks what happened on that day, and he reveals it's about the day he met her.
The next morning at the gallery, Dan and Serena wake up to real snow falling outside. He admits it's the best Christmas ever and they get ready to go home. At the Waldorf's, Eleanor is in the middle of escorting Jack out after spending the night together but is surprised when Harold and Roman come out of the elevator. Harold explains that their flight was cancelled due to the snow but that they have a hotel room. However, Eleanor tells them that they can stay at the penthouse, which they accept. Blair then comes downstairs and warmly tells Roman that she is in for a treat because Waldorf Christmases are like no other. At The Palace, Serena arrives home to find the tree inside the suite. She smiles as she realizes that was Dan's gift. At the loft, Dan enters to find Rufus making waffle batter. He explains how the tree delivery went but that Lily helped them a lot. Rufus says that he thought Dan mentioned she was out of the country, but Dan confusedly says that she, Serena, and Eric are going to see The Nutcracker the next day, so she isn't. Jenny and Alison come out to the kitchen and Rufus says that after they open presents, he needs to go to the gallery for a while. Alison suggests that while he's gone, they can drink hot cocoa and watch a movie, and maybe go for a walk later. Back at the Waldorf's, Blair, Eleanor, Harold, Roman, and Dorota open gifts together. Blair is surprised with a beautiful coat and she gives Dorota a BlackBerry so they can text. Back at the loft, Rufus is gone and Jenny asks Alison if she's going back to Hudson. Alison confesses that she is but that they're all going to be okay regardless. At The Palace, Bart joins Lily, Serena, and Eric for present opening. He tells Serena and Eric that he has deep feeling for Lily just as her phone starts ringing. Lily goes to answer it but Bart says she won't want to interrupt the moment. He then gets on one knee and proposes to her. Meanwhile, Rufus is standing outside the hotel and leaves Lily a voicemail, saying that Alison is leaving and he misses her. Back at the Waldorf's, Blair receives a text from Chuck in response to her plea. He asks who he would tell, and attaches a photo of him and Nate in Monaco.
- Blake Lively as Serena van der Woodsen
- Leighton Meester as Blair Waldorf
- Penn Badgley as Dan Humphrey
- Chace Crawford as Nate Archibald (Credit only, as he does not appear in the episode)
- Ed Westwick as Chuck Bass (Credit only, as he does not appear in the episode)
- Taylor Momsen as Jenny Humphrey
- Kelly Rutherford as Lily van der Woodsen
- Matthew Settle as Rufus Humphrey
- Connor Paolo as Eric van der Woodsen
- Margaret Colin as Eleanor Waldorf
- Zuzanna Szadkowski as Dorota Kishlovsky
- Jessica Szohr as Vanessa Abrams
- Robert John Burke as Bart Bass
- William Abadie as Roman Garrel
- John Shea as Harold Waldorf
- Susan Misner as Alison Humphrey
- John Dossett as Jack Roth
- Austin Lysy as Freddy Parnes
- Derek Cecil as Alex
- Santa Baby by Constance Billard Choir
- O Christmas Tree by The Plush Interiors
- Christmas Alphabet by The McGuire Sisters
- Christmaskwanzakah by The Dan Band
- Deck The Halls by The Republic Tigers
- The General Specific by Band of Horses
- All That I Want by The Weepies
Serena: I need a gift idea for Dan now that Vanessa got him the most thoughtful Dan-like present ever.
Blair: Why don't you buy him a new outfit for Cedric and call it a day?
Rufus: Would you have come back if Jenny hadn't shown up to bring you?
Alison: If I hadn't, would Lily be here right now?
Rufus: I guess by turning our backs on these other people we thought we could fix ourselves.
Alison: Maybe other people aren't the problem. Maybe we changed.
Rufus: And at what point do we admit that no matter how much we want it, or how hard we try-
Alison: It's just not working.
Dan (on gifts for Serena): A year of cheese for $600, are these people kidding? I could a buy a cow for that much money and make my own cheese.
Jenny: You just said "make my own cheese." That's disgusting.
Roman: Eleanor, we've been friends for a long time, since before Marc Jacobs went into rehab.
Eleanor: Friends don't steal other friends husbands.
Blair (to Vanessa on her helping with Dan's gift): Serena must be so grateful because she likes to see the best in people. I like to see the truth.
Eric (on Bart): He only has one facial expression. He scares me.
Serena: And he raised Chuck, that scares me.
Eleanor (to Harold on Blair): Blair learned scheming from her mother and unrealistic dreaming from her father. She tries really hard to act all grown up but don't you be fooled. She's still a little girl... who needs her daddy.
Serena: This is your story.
Dan: It's the original. Right out of the spiral notebook.
Serena: I'm kinda scared to read it. What happened on October 8, 2005?
Dan: I was accidentally invited to a birthday party. Where I met a girl. She only spoke two sentences to me but I've never forgotten her.
Serena: Wait, your story is about me?
Rufus (over voicemail): Hey, Lil. You know, everything's closed on Christmas. Diners that claim to be open 24/7... it's false advertising. So, uh, Alison's leaving. She's spending time alone with the kids and I seem to have walked all the way from Brooklyn to your doorstep, without a jacket, in the snow. So what the hell. I miss you. And I have been missing you for a while.
- The episode title is based off the movie Roman Holiday.
- This is the first appearance of Harold in real time, not flashbacks.
- Jack Roth, the man Eleanor meets, is never seen or mentioned again after this episode.
- Patek Philippe watches, such as the one Serena buys Dan, retail for anywhere from $12,100 to over a million dollars.
- This is the only episode where Vanessa, Eric, or Lily is seen in Blair's bedroom.