She's Having a Maybe is the second episode of the first season, and the second episode overall.
As Zoya cautiously explores a new romantic interest, Max tears down boundaries in pursuing one of his own. At a black-tie affair, Audrey struggles with her mom, Kate works overtime, and Julien vows to fix her mistakes once and for all.
Kate Keller prepares herself for the annual parent-teacher conferences, whose new heels are noticed by her friends. She finishes her latest GG post, but is warned by Jordan Glassberg to put it away. Davis Calloway arrives and is greeted by Headmistress Burton - the teachers discuss his achievements, including the underwriting of the art scholarship Zoya Lott holds. Jordan recommends tagging him to a blast about it, reminding her Gossip Girl hasn't posted in days. Kate needs time to verify all her tips and can't risk anything - she's informed by a female teacher two students actually raised their hand today to Kate's glee. Jordan hides Kate behind him as she sees the students handing out at Dumbo, having not invited Zoya.
At home, Nick Lott informs his daughter that he's off to meet her teachers, and that she's still grounded. He knows she feels bad, terrible even, but she has other worries - the headmistress asked to personally meet with Nick, presumably about the scholarship. Zoya checks Julien's Insta stories.
Inside the elevator elevator, Julien worries about Obie's absence in her life, but is assured by Monet that with a series of posts and hashtags, she has at best 2 days to get him back together. Luna reminds him it'll be like that time she accidentally took a selfie behind a homeless camp and wore a "Bernie babe" tee for a week. Julien strongly believes apologizes to Obie profusely can win him back, but Monet and Luna are not as inclined.
Audrey is coming down a flight of stairs and finds a bored Max. She remarks he isn't bored by uninspired. He says she is one of the last people in the place he doesn't know intimately - she rebukes he close his eyes and pretend someone's new. Max tells her he doesn't need to fantasize about anything, for he allows himself to sample everything. Aki appears, with Max seductively suggesting there are nerve endings two hands alone can't stimulate. Aki turns him down. The elevator opens, where one of the teachers, Rafa Caparros, gets off with another man. The three notice that, with Max choosing to go and investigate why he ditched parent-teacher night. Audrey suddenly gets in email from the school that her mother, Katherine, never showed up to Audrey's irritation. Aki suggests she had a good reason. "Like all the other times," his girlfriends finishes in a disgusted tone, sending herself into a rave about how she doesn't give a shit. Aki urges her to give her mother sympathy, since "Kiki" is going through a divorce and her line is failing. Audrey refuses to listen.
She heads to the rest of the girls and briskly takes Luna's phone to take a picture of the three, before pulling Julien away. Monet posts it, telling Luna that #Jobie needs to get back together or she can kiss an Edelman summer internship goodbye, since Julien's followers are bolting. JC confides in A that her followers are asking where Obie is, having not realized how invested they were in her relationship and assumed they were only there for her. Audrey sarcastically says that's the problem with her, but apologizes for her snarky reply since Aki pulled a logic comeback at her. Julien asks what's up but Auds isn't up to talk about her mom. She says that just because she doesn't have a mom, doesn't mean she can't talk about Audrey's mom with her (plus she likes to like vicariously through fights she never got to have). Audrey confesses her mom's absence tonight and predicts she won't show for tomorrow's fundraiser. Julien comforts her upset friend, noting Audrey knows she's worth showing up for. A says they have to get back to the others, but Julien informs her they're still on Zoya's case. She bemoans how she knew they wouldn't be instant family but that she isn't a bad person nor has she done anything wrong. Luna disagrees, but Julien says no one has seen Zoya lately while she's giving Obie space. Julien asks Aki if Obie is meeting him tonight, but is informed he isn't. Monet urges her to accept he's not in her orbit anymore, but in Zoya's. Luna shows her phone, where Obie has liked their photo. Julien excitedly texs him, but O replies he's going to bed. Obie is seen getting off a subway station, sending a quick text to an unknown person if they're around.
In the bathroom, Max casually remarks it's nice not have to wait for the straight guy gap to Rafa. The latter is annoyed, telling him this is widely inappropriate. Max says he isn't looking but takes a quick peak nonetheless. Rafa zips himself up quickly as Max compliments his size. He asks why he isn't at parent-teacher night sucking up to his dads. Rafa says electives teachers aren't required to participate - Max pipes up that he likes to watch then. He then proceeds to boldly proposition Rafa whom replies he doesn't fuck his students. Max replies he'll top then then. For his sake will Rafa pretend this conversation didn't happen. He leaves but Max grabs his drink and intents to follow him, but it stopped when a guy asks him if Rafa Caparros just passed. He brags about how he couldn't walk for a week and didn't want to, while his companion states Rafa is the fuck of New York. He tells Max to read all about ti on MaleGeneral, before adding Max himself is mentioned - briefly to boot.
Zoya meets with Obie outside her building, telling him she thought he was joking. Obie says he went out for a walk a couple of hours ago, and just stopped now. "What if my dad sees you?" she asks, but she's assured freshmen are last at the conference. She says its still risky, noticing her doorman looking at the pair. She grabs his hand to pull him to the side, blushing when she realizes what she just did. She compliments how big his smile is, and they both laugh. He remarks how he's barely seen her at school, but is informed Zoya's been trying to keep a low profile not because of Julien but for herself. Suddenly conscious of possible spies, Z states she should head back inside but Obie comments its only the Upper West Side. Zoya catches his brief moment of privilege, but both state they like it up here. Suddenly, a girl walking her dog snaps a photo of the pair before they depart.
Kate walks into the teacher's lounge, complaining to her colleagues about how late it is plus the audacity of a mother who says her son should be allowed to vape in class. Kate gets another notification from the Gossip Girl account, shuffling through questionable tips before arriving at Zoya and Obie's picture. She quickly types up the newest blast before being interrupted by Nick, whose looking for Ms. Keller. Replying this is her, Kate posts the picture before going with Nick. In the hallway, the air are seen by Davis.
The teens receive Gossip Girl's newest post. Aki says they're allowed to hang, but Monet interjects that although he said he was going to bed he didn't say with who or where. Audrey asks Monet if she's trying to incite a riot, but she is determined Julien squash Zoya like the queen she is. Julien says they don't do hierarchies, but Luna says that's because everyone knows whose on top. Monet, impatient, grabs Jules' phone and shows her a photo of her and Obie, giving her the idea to post it and pretend he's with her right now. She captions it "Don't believe the gossip girls because I am the one with the truth."
At the conference, Nick tells Kate she hopes she's liking Constance, given she didn't like her old school. Kate's phone rings, but she tells Zoya's dad one of her favorite things about her is that she's one of the only students who seems happy to physically be here. He phone continues to send her notifications, to the point if Nick asks if she needs to get it. Kate replies yes, to make sure it isn't the police or her mother. She sees the comments berating Gossip Girl as a liar and a fraud, and checks that her follower count has fallen. A smile plastered on her face, she asks where were they.
Audrey thinks Crisis "O" has been averted. Monet's happy to report the 'Ju-liens' are mauling GG and hopefully the bitch will be spammed out of existence more swiftly than Scooter. Luna's advice is while GG is down for now, the next picture of them she won't be able to spin. Julien asks what she's saying, but Monet makes it clear it's either her or Zoya. Julien is unwilling, but Monet presses on no one follows a brand ambassador for failure while Audrey says she has to do it for herself.
The next morning, Audrey wakes her mother awake. She shows off a dress she rented, one Kiki wore. Kiki asks if anyone died, causing her daughter to snidely say her closet. The now ex-Mrs. Hope tells her it's too early for jokes. Audrey asks why she didn't go to the parent-teacher conference. Staggered for a second, Kiki lamely states she couldn't go. She says Audrey been going there since kindergarten, and she gets the same "Audrey is brilliant" and "Audrey is wonderful". Her daughter wonders if she likes hearing those things. Kiki says she does. Audreys wonders if perhaps she might wear the dress tonight for the Black Tie School Supplies fundraiser. However, Kiki can't - she has a dinner and already donated. Audrey pleads with her mother, saying she's school chair and it's important to her. She asks if her father will be there, Audrey responding she didn't invite him, or her. Kiki laments how she used to be her assistant, how she came to their dinners, vacations, and told her "I wish I had a family just like yours" before stealing it. Audrey understands, but she wanted her mom to know only she will be there, and begs her to come. Finally, Kiki relents before going to sleep.
At the Lott household, Nick mentions all her teachers like her, especially Ms. Keller. Zoya says she's great, but asks about Headmistress Burton. Nick revels the school board thinks a scholarship scandal given the student in question would be less than ideal, but makes it clear she is still under strict probation. He warns his daughter they'll find any reason to remove her, and she promises she'll be perfect. Nick wants to define the word, showing her the Gossip Girl account on his phone. Zoya says Obie showed up unannounced. Nick reminds her not to be distracted form anything that'll keep her head down.
Kate arrives at work exhausted from no sleep, a fact noted by Jordan. Kate reveals that they flagged all of the photos on the account as inappropriate, they being Julien's fans, the 'Ju-lions'. Jordan compliments them as clever, but Kate is annoyed she's being tagged in the same overused meme. Kate's desperate to get in control again, mentioning that Martine is struggling to find a job elsewhere. Jordan assures her nothing's been objectionable and the account will be unlocked for her by the end of the day. Kate rants about how Gossip Girl's voice is itself a lot of work to figure out, but he orders her to relax and get to class. He urges her not to give the game away, as they're just entering their first test.
Jordan and Zoya stare at each other from across the street at the entrance of the school, but Audrey pulls the former away and excitedly notes how she defeated Gossip Girl, how her mom is coming to her event. She is distracted by Aki scrolling through shirtless pictures of their classics teacher. Her flustered boyfriend explains Max has set his next target, hoping to huff and puff and blow him. Max recognizes a towel on a photo as those belonging to Tenth Street Baths, a men-only bathhouse. He asks Aki to accompany him to Audrey's distaste and the latter's verbal denial, but sees through his internal want. He walks away as Julien says she'll look for Obie, avoiding an approaching Zoya.
Audrey reluctantly admits Aki was right about Kiki still being upset about her father but refuses to listen to his advice, insisting she's taking care of it. She asserts her mom will hope to the fundraiser and her father won't. Next to her, Julien spots Obie staring at Zoya. Stopping him from getting to the courtyard doors, Julien tells him she received his message and confesses she was petty, cruel and jealous for no reason. Julien says she's ready to end this "break" if he is, but Obie makes it clear they broke up, even if she didn't. He admits he cares about her, but the rest has been done for a long while. He leaves her in tears to go to Zoya, whom he tries to ask out. However, the girl says that although she wants to hang, her father's words remind her it's not a good time. Obie restates that, although having been afraid to say it out loud, he's been free and wants to spend it with her. Zoya wants him to know she can't do what she just wants since. Obie asks if she'd go out with him in a world without sisters or scholarships, to which she says yes if people wouldn't know, but that's impossible. Obie compliments her smile and leaves.
Having seen the conversation, Audrey condemns Obie for consorting with the enemy and says they can cut him out, despite Aki objecting. Julien bemoans she never wanted Obie out of his life, despite Audrey says she should and an approaching Monet say she can't. She begs Julien to tell her they made up. Julien sadly informs her #Jobie is done for good. Monet says she has no pleasure to say this, but Luna interjects that Phase One, ending Gossip Girl, is done and now they have to move on to Phase Two, Zoya and recommends banishment. Julien blames herself for brigning her but banishing her would simply make Obie pine after her. However, she reasons that although he's interested in her, what if they drive him way instead of vise versa? She ends her epiphany by making a deal with the devil herself, Gossip Girl. Monet warns her she's cancelled, but Julien says she'll uncancel her only if they get her the juiciest dirt on Little Z. "GG works for me now," Julien brags.
In the bathhouse locker room, a sad Aki complains about Audrey's distance to a now nude Max. However, his friend doesn't want to hear it. "We're here to cruise," he says as he throws him a towel to hide his member. Aki tells him he's stalking a teacher, but Max retorts that a man wants to be found with his bi-weekly bathhouse selfies. Aki can't believe Max got him into this, just as Rafa exits a room and stares at the both of them before entering a sauna. Max asks if he has his consent, to do whatever. Aki understands he wants to make Rafa jealous as the latter peers at them through the window. Gathering up the courage, Aki kisses him. The two make out and create a scene that Rafa annoyingly rolls his eye at. They break apart, and Aki timidly asks if it worked. Max, looking down, says it worked better than he imagined. Rafa confronts them, demanding if they want to get him fired. Rafa scolds the two that they shouldn't be doing this. Max clarifies if he's not interested, or is. A pregnant moment passes, with Rafa saying they should be in school. Max says likewise, causing Rafa to furiously storm away. Aki asks if they should follow him and do it again.
Jordan tells Kate there has to be something they can give Julien but Kate denies it, glad because they doesn't want to destroy Zoya. Jordan insists they have no choice; Reema perks up and says they should post something dirty to distract them. Kate sarcastically asks what, complaining of the lame tips they've received. She declares if they don't give Julien what she wants, that's it. Zoya suddenly appears, saying she was told by the Headmistress to report for volunteer duty. In the library, Kate lightly jokes of the many hyphens in everyone's name. She notes that "Zoya" means "life", and asks about Kate's name, which means "pure". Zoya says it fits her, but Kate says she doesn't know her very well. Zoya says just in the last hour, she's come to know her better than everyone else. The teacher asks about Julien, but Zoya says she doesn't know her at all.
- Jordan Alexander as Julien Calloway
- Whitney Peak as Zoya Lott
- Tavi Gevinson as Kate Keller
- Eli Brown as Obie Bergmann IV
- Thomas Doherty as Max Wolfe
- Emily Alyn Lind as Audrey Hope
- Evan Mock as Aki Menzies
- Johnathan Fernandez as Nick Lott
- Laura Benanti as Kiki Hope
- Adam Chanler-Berat as Jordan Glassberg
- Zion Moreno as Luna La
- Savannah Smith as Monet de Haan
- Jason Gotay as Rafa Caparros
- Kristen Bell as Gossip Girl’s voice
- Donna Murphy as Headmistress Burton
- Megan Ferguson as Wendy
- Rana Roy as Rima
- Luke Kirby as Davis Calloway
- Bruce Faulk as Jimmy
- Jared Reinfeldt as Victor
- Charles Oduro as Matt
- Gart Littman as Doctor
- Cedric D. Cannon as Store Owner
- Kirsten Maxwell as Zoya Lott Double
- "Spotlight" by Jessie Ware
- "Jaguar" by Victoria Monét
- "All That" by Emotional Oranges
- "Are U Down" by Jayda G
- "Run The Track" by Cosha
- "Dora" by Tierra Whack
- "Freak" by Doja Cat
- "Put Your Head On My Shoulder" by Paul Anka
- "Someone Ain't Right" by Doris Troy
- "My Baby Just Cares For Me" by Nina Simone
- "Our Delight" by Roy Haynes
- "Tears To Burn" by Dinah Washington
- "The In Crowd" by Ramsey Lewis Trio
- "Saturdays" by Twin Shadow & HAIM
- "Once Upon A Time" by SHAED
Gossip Girl: Good evening, followers. Gossip Girl here. Your one and only source for the truth behind the scandalous lies of New York's elite. What's all that rustling reverberating through the twilight? Why, that's the echo of anxiety, the jangling of nerves in preparation for a big night ahead. And what exactly is on the docket this September evening? An autumn equinox affair? Opening night at the ballet? Or something more essential? Annual parent-teacher conferences. But on the Upper East Side, they do things differently. The students aren't the ones under review. It's the teachers. While the parents play with the politics of privilege, where are their heirs? Deep in Dumbo, of course. Looks like somebody wasn't invited to the party.
Gossip Girl: Good evening, followers. Gossip Girl here. Back with a vengeance, and not a moment too soon. Are you primped and prepped for the night's philanthropy? Due to recent events, I'm feeling a little less than charitable myself. But I never like to spoil an appetite before dessert. Revenge is a dish best served bold, after all. So while you pretend to be touched for your 1040s, I will be right behind you, your own Internal Revelation Service, waiting to bring you in and take you down. Think you burned me? Think again. Watch the skies. I'm coming.
Gossip Girl: Spotted. Noble O and Lil'Z ditching the big event for some late night charity of their own. Has the unthinkable occurred? Has JC been officially subbed out for her Samaritan sis? Or is this just another twist in their Upper East of Eden? Your move, JC. Better check your mate before she takes your king.
Gossip Girl: You often hear it said, "People don't change." They can grow, they can learn, but change? Not gonna happen. Why do we tell ourselves this? What safety is there in clinging to the belief that what makes us who we are needs to stay the same forever? The world around us changes each second. And yet...we're slow to accept we have to do the same. But just as every maybe transforms into a yes or no, eventually...things do change. And we do, too, whether we want to or not. A word of warning, though. Now that I've changed into who I was meant to be, I'm watching even more closely. So don't go changing to try and please me. I see you just the way you are. And I'll make sure you see it, too. That's what friends are for. XOXO, Gossip Girl.
- This episode's title references the 1988 film, "She's Having a Baby".
- The film revolves around a picturesque couple attempting have a family of their own, but in those struggles the husband begins to question his commitment to his wife by thinking about another girl romantically.
- Alec Baldwin is mentioned to have confiscated Jordan Glassberg's phone during a previous PTA meeting. Alec Baldwin's brother William Baldwin portrayed Serena van der Woodsen's father, William van der Woodsen, in the original Gossip Girl series.
- Dumbo, a neighborhood in New York, is seen. This was previously the hometown of Dan Humphrey, with the subway tunnel that Obie Bergmann IV exits being one that was seen repeatedly in the 2007 series.
- In an interview with Town & Country Magazine, showrunner Joshua Safran commented Dumbo saying, "In the original, Dan was the poor kid and he lived in Brooklyn, which was ridiculous then, of course.... And now the richest character of our show lives in Dumbo."