Crazy Cupid Love is the 15th episode of the fifth season and the 102nd overall.
Another picture perfect Valentine's Day on the Upper East Side. And how am I going to celebrate? By exposing a giant secret today that's sure to break more than a few hearts.
It's Valentine's Day on the Upper East Side and Blair can't resist playing cupid for someone she loves. Georgina is intent of stirring up more drama, so she decides to crash Nate's Valentine's Day party. Meanwhile, Serena is shocked by something she witness at the party.
Blair has returned from her honeymoon and brought along her new social secretary, Estee, who is employed to escort Blair on all public outings and read her mail. Estee says that Blair's first official public appearance will be that evening. At the VDW's, Rufus is meeting with a Cartier salesman to pick out some jewelry for Lily to celebrate Valentine's Day. Dan arrives and asks if she'll see it but Rufus assures him she's in Washington DC at a fundraiser luncheon. The salesman asks if Dan wants to buy anything but Dan says he's single and only came by to pick up some Blu Ray DVDs to give Blair, since she's home now. Rufus replies that now that Blair's a married woman, it might be time for Dan to move on. Dan thanks him for the advice but continues that he's only trying to be a good friend. Outside The Empire, Chuck and Serena are on the phone discussing how they're not into Valentine's Day this year. Chuck then bumps into a guy on the street. After they hang up, Serena goes downstairs to leave when she runs into Blair, who is excited to see her. Blair says that she's mad at Serena for releasing the video at the wedding and Serena is mad at her for running off at Dan, it cancels out so they can forgive and forget. Serena says she didn't release the video and Blair thanks her for taking the fall for her and Chuck. They decide to forgive each other and Serena tells Blair she's planning to spend the afternoon interviewing a celibate seventy year old lady for her "All The Reasons I Hate Valentine's Day" column. She's about to say she hasn't had a good Valentine's Day since high school with Dan when he arrives in the penthouse. She leaves and Dan hands Blair the DVDs. He offers to come over later and watch them with her but she explains that she already has plans for the night. She tells him to find plans and he also mentions that his last good Valentine's was in high school with Serena. He then leaves to meet Alessandra. Once he's gone, Blair tells Dorota she's planning to get Dan and Serena back together.
Elsewhere, Nate calls Lola. She asks how he got her number and he says he offered her boss some free advertisement space in The Spectator for it. He asks her out but she declines, saying it's too cheesy to go out on Valentine's for a first date and she has to work anyway before she hangs up. Nate's assistant, Tina, overhears the conversation and then heads out to her computer, where she joins a four way video chat with the guy who bumped into Chuck, the Cartier salesman, Blair's doorman, and Georgina. Georgina asks if Tina has any good gossip because all she has is a princess under surveillance (Blair), a dog lover who hates the holiday (Chuck), and a lonely boy with no plans (Dan). Tina says no, since Nate can't even get a cater waiter to go out with him. Frustrated, Georgina says Gossip Girl is failing under her control and she needs a scandal to end all scandals to save it. Philip suggests blackmailing Dan with the information that he sent the video in, but Georgina says that would only work if she loads him up and everyone is together when he detonates. Philip remarks that it's too bad they can't all just go back to high school. At The Spectator, Tina goes into Nate's office and demands to know why he didn't tell her about the party. Nate asks what party, and Tina says Gossip Girl posted that he's hosting the Come As You Were party, a throwback to high school. Nate says he's not throwing a party and it's a joke, and Tina says that's probably a good thing since they couldn't get a caterer this late. Nate realizes it's an opportunity to see Lola again and decides to have it anyway. She then texts Georgina that the plan worked. At the VDW's, Ivy (who is still posing as Charlie) arrives. She runs into Rufus and says she's only in town for a few hours before heading to Europe. Rufus says Lily isn't home yet from DC but she would love to see her, and Ivy says that she wants to explain why she left so abruptly to her. He offers to let her sit and wait for her, which she does while Rufus goes to run errands.
Meanwhile, Serena is waiting at a restaurant for her interviewee when she sees Dan, also alone, waiting for someone. They pretend not to see each other at first until Dan goes over to say hey. She explains she's supposed to be meeting with an elderly celibate woman to interview and Dan says he's waiting for Alessandra. A waiter then comes by and offers them a complimentary glass of Dom champagne, saying it's a Valentine's gift for their customers. In the bar, Blair and Dorota are disguised and spying on them. Blair announces it's time for step two and they leave. At The Empire, Nate finds out there's a note in Lola's file barring her from working any events hosted by The Spectator. Chuck offers to host the party at The Empire in their suite so Nate can see Lola again. Back at the restaurant, an elderly couple tell Dan and Serena make a lovely couple before mentioning they've spent fifty four wonderful years together. Immediately after, the waiter comes by with desserts for the two and again says they're complimentary. Dan realizes no one else has the dessert and Serena mentions that it's weird neither of their meetings showed up. Dan and Serena check their messages and discover 'someone' called both Alessandra and the virgin cancelling their meetings. They both realize Blair did it. At the Waldorf's, Blair is picking out a dress for the evening. Dorota says the plan is going very well and Blair says the next step is finding a way to get them together at Nate's party. She then gets a text that the party was moved to The Empire, and realizes she can't bring Estee to Chuck's hotel. She instructs Dorota to go and play Cupid in her place but Dorota is convinced it's a bad plan. At Georgina's, she also finds out the party was moved. She becomes disappointed because Blair most likely won't be there and therefore the Dan-Bomb is useless without her. She then gets a call from Blair's doorman and informs her the VDW's doorman found something she might want to know. At the VDW's, Ivy is on the phone asking if someone has noticed she's gone. She tells them to tell that person she'll be back in a couple hours and hangs up just in time for Georgina's arrival. She demands to know what she's doing back in the city and Ivy says she's just in town for a brief visit and no one should know except Rufus. Georgina asks for some gossip but Ivy swears she knows nothing other than Blair and Louis signing a prenuptial. She then leaves and calls Philip, and tells him to find out who represents the Grimaldi's legally and to meet her there, and that they might need to file for divorce.
At the Waldorf's, Blair asks Serena how her meeting was. Serena says she knows she set her up with Dan, and Blair insists she's just trying to bring love to her friends. Serena argues that Dan doesn't have feelings for her, but Blair says Dan also said his last good Valentine's was in high school with her. Serena says it wouldn't work and Blair invites her to attend the Cardiac Ball with her. Serena declines and says she would rather work on her blog, writing how true love is nothing but a myth. At The Empire, Dan goes to see Nate. He says he can't make it to the party, and Nate is disappointed since Chuck, Blair, and Serena are also not coming. Dan explains that Blair is trying to get him back with Serena and it reminded him he didn't have a good high school experience. He then get a text from Gossip Girl telling him to bring Blair to the party. He replies asking why he would do that and she replies that if he doesn't, she'll release the video he sent in. He then tells Nate he's coming to the party now. Elsewhere outside, Rufus gets a call from Ivy asking where Lily is. He says her train got delayed and she's headed straight for The Empire, which is where she's meeting him. She asks if she can come by on her way to the airport and he agrees to tell her she's on her way. At the Waldorf's, Dan goes to see Blair and tells her he thinks there might be hope for him and Serena. Blair directs him to ask her to Nate's party but he suggests she come with them to ease the pressure of a real date. She says no, since she has Estee. Dan says it's a good idea if she comes because then she can see Chuck isn't a threat and Nate says he probably won't be there anyway. Blair agrees to do a quick swing by. While leaving the penthouse, he sends a text to Gossip Girl saying it's done. At Georgina's, she and Philip are going through Blair's prenup. Georgina discovers that if she defaults on the marriage in the first year, the Waldorf's will go bankrupt with how much money they'll owe the Grimaldi's. Georgina announces she's going to show the world what Blair really thinks of her vows by using Dan.
That evening, Blair, Serena, and Estee arrive at The Empire for the party. Serena asks why she's dressed in her school uniform and Blair replies that she has a special surprise for her. When they reach the suite, they run into Chuck (who is wearing his signature scarf from season one) on his way down. Estee, upon surveying the scene, decides to go downstairs and keep an eye on Chuck. Nate runs into Lola and says the party isn't at The Spectator and maybe she can see his world up close without being overwhelmed and she isn't missing work. Meanwhile, Dan arrives dragging Ivy, who he saw and knew Serena would want to see. Serena asks where she's been and Ivy says she just felt guilty about the car accident and went back to Florida. Serena says she won't find out what room Lily is in until Ivy tells her all about the past few months and what it's like living with Carol again. Elsewhere, Blair pulls Dan aside to help give him the outsider look Serena is drawn to. She suggests he take Serena somewhere quiet but he says he doesn't think he can go through with it. Blair tells him not to worry since Serena already likes him and as long as he's as good with her as he's been with Blair all year. Dan then gets a text from Gossip Girl telling him to kiss her. He goes to find her and Blair asks Serena if they can talk. Ivy is then approached by Lola, and calls herself Charlotte Rhodes, before asking if she remembers her from the acting class together in Florida. They both ask each other what they're doing there. Elsewhere, Blair tells Serena that Dan is looking for her and her surprise was that he thought their lunch date went great. Dan texts Gossip Girl, and hears a phone ring at the same time. He sends another and follows the ringing. He opens the door to Chuck's room to find Georgina. She denies being Gossip Girl, but he sends another text and her phone rings. She claims to work for Gossip Girl, but that the job was harder than she thought. Dan says that if she ever reveals he sent the video, he'll tell everyone she works for Gossip Girl. She replies that she was only trying to help them since their tension is boring to watch without action. Blair then enters and asks what's going on. Dan says she was just leaving, which she does. She hands him back his tie and asks if he really wants to get back together with Serena. He asks if she really wants them to get back together, and Blair admits she only wants him to be happy before asking what would make him happy. He kisses her passionately, during which Georgina takes a pictures and Serena witnesses.
Downstairs, Chuck is approached by a drunk Alessandra, who attempts to flirt with him. She asks him if they could hook up, but he declines and leaves. Estee sees the whole thing and texts Blair that it's time to go. Upstairs, Blair tells Serena she was only trying to get them back together and it's not her fault Dan kissed her. Serena says she sounds like she's still in high school and maybe they shouldn't talk before leaving. Estee then enters the suite and tells Blair it's time to go. In the living room, Lola explains that Carol didn't support her being an actress and so she's secretly living in the city and working as a cater waiter to make ends meet. She asks if Ivy is working and she says yes, but that she got one part that paid well but took longer and was more complicated than she thought. Nate comes by and says they look so alike they could be sisters, and Lola says her mom used to say the same thing. Ivy excuses herself and leaves, while Nate says Lola owes him an apology since she knew someone at the party in his world. She asks why Ivy Dickens was there and Nate says she's his friend's cousin and her real name is Charlie Rhodes. Confused, Lola asks about her real name and Nate explains that her mom is a crazy woman from Florida who made her go by Ivy Dickens but now she gets to go by her real name. Lola again asks if he's sure it's Charlie Rhodes and Nate says yes. By the elevator, Dan has taken Georgina's phone and threatens to smash it unless she deletes the picture. She says she already emailed the picture to herself and Dan says if she does anything with it, he'll out her as a Gossip Girl Spy. Georgina confesses that she is Gossip Girl and that what she set in motion is more important than any picture. She continues that Dan now knows Blair likes him back but they can't do anything about it without ruining the Waldorf's family future. She finishes that if Blair used to hate him for being poor, how much would she hate him for making her poor too? Back downstairs, Georgina finds Chuck and shows him the picture of Blair and Dan. Outside, Dan catches Blair before she leaves. He asks why she didn't tell him about the prenup and she says she can't risk her family's future and her feelings for Louis are all business. Dan says she kissed him back, but she answers that she would never do that to Serena and leaves. Back at her home, Georgina tells Philip she doesn't want to ruin being Gossip Girl over one photo and that if she waits it out, it won't be long before they're doing worse things than kissing. At the Waldorf's, Blair and Serena open the door to their shared bathroom and close it, not wanting to speak. Outside, Dan is walking when he steps on a candy heart, breaking it. At The Empire, Chuck is hooking up with Alessandra while telling her he's interested in her work. He asks her what it's like working with Dan. Back at the Waldorf's, Estee is preparing to leave when she sees a framed photo of Blair and Louis on the piano. She covers the photo of Blair, leaving only Louis smiling at her from the shot, revealing she has feelings for him. Also outside, Lola searches for Charlotte Rhodes on Facebook and finds a profile with Ivy's photo attached. She sends a friend request. Meanwhile, Ivy arrives back in The Hamptons and tells a nurse she didn't finish her errand. Ivy asks how she is, and the nurse replies that she worries there isn't much time left. The nurse says Mrs. Rhodes really cares about her and says she's up if Ivy wants to see her. As she leaves the room, a photo is shown on the nightstand of her and CeCe.
- 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
- Kaylee DeFer as Ivy Dickens
- Kelly Rutherford as Lily van der Woodsen (Credit only as she does not appear in the episode)
- Matthew Settle as Rufus Humphrey
- Michelle Trachtenberg as Georgina Sparks
- Zuzanna Szadkowski as Dorota Kishlovsky
- Ella Rae Peck as Lola Rhodes
- Nick Cornish as Philip Becker
- Cruel by St. Vincent
- I Got It From My Mama by Will.I.Am
- Cheerleader by St. Vincent
- Let's Get This Party Started Right by Tag Team
- The One You Say Goodnight To by Kina Grannis
- Baby Says by The Kills
Dorota: I was worried you'd be locked away in big stone tower somewhere and only way to speak is through smoke signals or coded messages on Twitter.
Blair: Thankfully, Dorota, we don't need to learn Navajo just yet.
Random Man (after bumping into Chuck): I'm sorry.. have a good day.
Chuck: I doubt that.
Blair: I want to up my royal status from princess to queen... of hearts!
Georgina: Under my stewardship, Gossip Girl is but a shell of her former self.
Georgina: It was so much easier to stir stuff up when we were all in high school and in the same place all the time!
Ivy: I can't believe Blair went through with her marriage to Louis, I really thought she would end up with Chuck.
Rufus: Between us, I think she may have wanted to.
Dorota: Operation Derena going very smooth.
Dan (on not coming to Nate's party): If it makes you feel better, I will totally sign your yearbook.
Nate: No, it doesn't.
Georgina (to Dan on Blair): The fact that you haven't done her already would be surprising if you weren't, well, you.
Serena (to Blair): They say people keep fighting about the same things until it tears them apart. You know what? Maybe we're there.
- The episode title is based off the movie Crazy, Stupid, Love.
- This episode hits series lows with 1.13 million viewers, a 0.5 rating in adults 18-49, and a 0.9 rating in women 18-34.
- Blair's side of the prenuptial agreement includes money, chateaus, real estate, yachts, jewels, and she owns half a museum.
- The song I Got It From My Mama by Will.I.Am is a tribute to the first season, first shown in Poison Ivy.