We open on Simon asking Lauren to get a parking pass for the new intern. Her name is Kelsi Lasker and Andrew recognizes the name because Lasker Lunch Meats is one of the agency’s biggest accounts. Sydney thinks just because she’s the daughter of an important person doesn’t mean she isn’t worthy. Zach jokes that she’s “championing the overprivileged.” Lauren then says that Kelsi owns a Mercedes with the license plate “Princes$.”
Zach and Lauren go into the elevator together but she’s worried that everyone will know they’ve been sleeping together. Lauren then tells Zach that she wants more but not from him. He’s relieved. When they get off Lauren makes like they just bumped into each other. As soon as she walks away, Simon asks Zach how long he and Lauren have been sleeping together. He warns him to tread lightly with office romances. Simon then asks Sydney how the new intern is doing. She tells him that she’s late. Then, Kelsi [played by Ashley Tinsdale] arrives and says she was late because of her “roommate drama.” Lauren then tells everyone that the meeting with the non-alcoholic wine people is in five minutes.
In the meeting with the non-alcoholic wine execs, Simon and Sydney tell them about the “habit loop,” which is about people having a habit they want to break. Sydney tells the execs that their product is “an extremely easy sell because it’s a healthy alternative to a habit they already have.” Meanwhile, Lauren and Zach are flirting with each other via eye contact. Then, Kelsi comes in to tell Sydney she has a phone call. She sees the wine and gets excited but disses it when she sees it’s fake. Sydney tells her to take a message to get rid of her but the execs want to hear her opinion on how to “make our product cool.” Simon tells them that she’s just an intern but Sydney says they should hear her opinion because she is their key demographic. Unfortunately, Kelsi just starts talking about her roommate problems which confuses the execs and horrifies the gang.
Zach suggests to Lauren that they go away for the weekend together. She declines saying he’s a habit she needs to break. When he walks away, Sydney comes over, says she overheard and asks where Lauren got the “willpower.” She says she realized she needed to break her “Zach habit” for something better for her. She then tells Sydney that she’s been meeting Andrew after work for coffee as friends and thinks she just needed “a cool guy to talk to.” Sydney asks if Andrew knows that she sees him as just a friend given he just broke up with Nancy and is vulnerable. Lauren is sure Andrew knows they’re just friends.
Simon and Sydney meet with Kelsi, who tells them that she knows she’s been screwing up. Sydney advises her to work on some things but Kelsi ignores her by texting, which Sydney mentions as something she needs to cut down on. Kelsi then says that it doesn’t matter how she does with the internship because her father will give her a job regardless, just like Simon gave Sydney her job. Sydney takes offense at her comment but Kelsi just laughs. Sydney then replies, “Listen you little twerking moron. I wanted to give you the benefit of the doubt but you and I are nothing alike. I earned this job and you don’t even try.” Kelsi then runs out. Sydney tried apologizing for going off on her but Kelsi tells her to “Go to hell” before giving her and Simon the finger as she goes down in the elevator.
The gang brainstorms how to apologize to Kelsi before she tells her father what happened and he fires the agency. Lauren sees that Kelsi just posted a picture from a frat party at Northwestern on Instagram. Simon, Sydney and Andrew head to the party. Andrew asks Sydney how long they’ll be there because he’s supposed to meet Lauren for coffee. She tries to talk to him about Lauren but Andrew thinks Sydney wants him for herself because of their kiss and says she better speak up now. Sydney apologizes to Simon for yelling at Kelsi but he replies, “I was about to snap at the little snot myself.” Sydney then wonders if people perceive her as a “self-entitled, very pretty brat.” Andrew replies that she’s none of those things and Simon says that she’s nothing like Kelsi and earned her job. She thinks he’s saying that because he’s her father. Sydney then sees Kelsi and apologizes again but she blows her off. Then, Kelsi challenges Simon to a game of beer pong, which he accepts. Sydney reminds him that he’s sober now so he says that he’ll play and she’ll drink. Kelsi ends up winning and Sydney gets really drunk. Simon offers to pay Kelsi even though interns don’t usually get paid but she says she doesn’t need the money and is about to call her father to tell him what happened. Then, Sydney has an idea. They can convince her troublesome roommate to take a smaller room in exchange for her not telling her father what happened. Kelsi agrees but doesn’t think they can get her roommate to agree.
The gang brainstorms on how to get Kelsi’s roommate to take a smaller room. Andrew throws out an idea, which Simon shoots down but Lauren thinks is good. Then, Sydney asks to see Lauren outside. She tells Lauren that Andrew clearly thinks they are more than friends and that she has to set him straight. Lauren then admits that after she has coffee with Andrew, she’s been hooking up again with Zach and that Zach and Andrew together make the perfect guy, “Zandrew.” Sydney tells Lauren she has to stop it before they find out about each other.
Zach and Andrew go to Lauren’s apartment. They know about each other and are mad. Lauren apologizes and asks if the three of them could go back to being friends and Andrew and Zach say they need time.
The gang plus Kelsi meets with her roommate, Brooke, to try to convince her to take a smaller room. They pitch that “older people like big things, but us younger people know that smaller is the place to be” and they give examples. Then, Brooke concedes that she’ll take the smaller room but then Kelsi jumps in and says she wants the smaller room. Then, Brooke and Kelsi get in a catfight, which the gang tries to breakup. Then, Kelsi’s father, Martin arrives, saying he came to take Kelsi to lunch. She tells him that the internship has been the worst experience of her life, how she was ordered around and got yelled at by Sydney when she said that she only has her job because her father gave it to her. Martin asks if this is true. Sydney admits that it is and Martin is glad and says, “You and Sydney grew up with every advantage. Unlike me, Simon raised a kid who gets it. She works hard and is damn good at what she does. I was hoping that a little time with these two people would rub off on you but…I guess I was wrong.” Sydney is ecstatic that Simon’s praise and says how it means so much coming from someone she barely knows. Simon says that he worries how people perceive him all the time. Sydney and the others say he’s a genius but he thinks they’re saying that because she’s his daughter and they work for him. But, then Brooke says that Simon seems cool and he’s happy. Then, Kelsi says, “But, you’re still old.” Sydney then tells Kelsi that she’s sad, takes a picture of her sad face and says she’s going to post it on Instagram. But, then asks Kelsi how to post it.