At the kid's school dance, Elena tries to appear popular in front of Syd, and chaperones Penelope and Max reach a milestone in their relationship.
Penelope is getting ready to leave on vacation with Max. Lydia tries to help Elena get ready for the dance but she says that she doesn't care about that sort of thing. Alex walks out in Berto's old clothes and says that he's going with an older girl, Emma. He tells them that she had a huge ask which is the way people ask people to go out these days. Elena says that she's happy that Syd doesn't care about that kind of thing. Suddenly, Syd walks in and begins performing a song for Elena and in the end asks her to go to the dance with her. Elena says yes. Penelope and Max are about to leave for Palm Springs when Schneider arrives with Nikki, one of the school's parents. She tells Penelope that she has to make up parent hours by chaperoning the school dance or pay a fine. Syd, Elena, and Alex arrive at the school dance. Syd says she can't wait to meet all of Elena's friends. Elena confesses to Alex that she lied and told Syd that she was popular. Max and Penelope arrive at the dance as chaperones. Penelope thanks Max for helping out and tells her about her homecoming. How she'd hid boxed wine in her shirt and got caught by sister Barbara.
Suddenly, Sister Barbara comes up behind Penelope and says hi. Max freezes up because he has a thing for nuns. Schneider and Nikki arrive. She tells Sister Barbara that Schneider is her boyfriend and that they are promised to each other. Sister Barbara gathers them around so that she can tell them their assignments for the night. She makes Penelope wear a gown over her dress since it's so revealing. Alex comes up with his date and introduces her to his mom. Penelope takes their picture. Syd and Elena jump into another groups picture and Elena pretends that they are her friends. Max calls Penelope from across the room and tells her that he can't stop looking at her in her nuns outfit. Before she hangs up, he tells her that he loves her which catches her by surprise. Doctor Berkowitz shows up having been called to help out. She has him take over the photo booth so that she can go talk to Max about what he said. But when she tries to get to him she runs into both Lydia and Schneider. Schneider is freaking out because Nikki called him her boyfriend. Penelope finally gets to Max but then a great song comes on so they both head out to the dance floor. Sister Barbara catches them dancing inappropriately. One of the teachers comes up to talk to Elena but she pretends that they aren't friends to impress Syd. Lydia's Shakira request comes on and she and Doctor Berkowitz dance together. Penelope takes Max to her favorite spot on campus. She asks him if he really said "I love you" on the phone and he says he did. He tells her that he's been thinking about it for a while. She tells him that she loves him too. She grabs a cigarette to celebrate but then throws it away when she hears someone coming.
Schneider pulls Nikki aside and asks her to get married. She says no that she just got divorced. He's hurt so he leaves but when Sister Barbara catches Nikki holding the discarded cigarette he comes back and tells the nun that they had had sex before. Elena and Syd are dancing when Syd says that Elena must be embarrassed by her since she hasn't introduced her to any of her friends. Elena says that that's not true but that she doesn't have any friends. Elena says she does have one friend and she introduces Syd to one of her teachers. Doctor Berkowitz tells Lydia that he broke up with Esme because he realized that he wanted to be with Lydia and that he doesn't want to spend his life without her. Lydia and Doctor Berkowitz decide to become friends again. Alex is upset because his date just used him to make another guy jealous. Max tells him that that's a good thing and that he should use that to his advantage. Penelope and Max dance together to a slow song. Penelope comments on how well he was with Max. Max says that Alex is a great kid and that he can't wait to have kids of his own.