The scene opens Aaron, Ben and Fitz at the gym and Aaron asks if he should pursue the relationship with Riley. Fitz says that he shouldn’t date within the group and asks Ben to back him up. Ben says that he shouldn’t do it. Sara texts Ben and asks to come over. Ben races home to clean up by throwing things in closed spaces. He tries to find a sexy pose to welcome her with and ends up naked with Radicchio covering his private parts. Sara comes in and averts her eyes and says that she should have been more detailed in her text. She sits down on the couch and tells that she has been seeing a guy named Matt. She works with him at the hospital. She gets distracted because Ben is still naked holding the Radicchio where his privates are. She continues to talk about Matt and says that he might be “boyfriend” material. She asks if he is offended since what they have going might have to end. Ben says that he is alright with it. She says that Matt and her are going to have sex. Ben says that it is all good because he is going to be having Colleen over. Sara says that she is a tease and Ben says that he is going to have sex with her tonight.
That night, everyone gets ready to go out for the night and the friends meet up at the bar. Riley says that she has to start her shift and Ben says that he has a date with Colleen. Aaron and Fitz tease him and ask what instrument is she playing now and Ben says that it is the bagpipes. Aaron says that he is going to ask Riley out and Fitz asks Ben and Sara to tell Aaron that dating within the group is wrong. They stumble over each other’s sentences and tell that it is a new world today and anything can happen. Aaron goes up to Riley, who is busy trying to memorize the drink orders. He smiles at her and she wonders why he is smiling. Later, Ben is on his date with Colleen and they are kissing. She tells that she wants to play. Thinking that she is into something kinky, he plays along. However, she wants to play the bagpipes for him. Meanwhile, Sara is on her date with Matt and they take their date to the bedroom and get busy. Back at Ben’s, Colleen is still playing the bagpipes. Back at Sara’s she is happy of what happened and goes out of the bathroom to find Matt quickly dressing. He says that he has work at home and has to leave.
The next day, Aaron goes up to Fitz and tells that he made progress with Riley. He tells that he asked her out and she said yes. Fitz tells that he needs to stop dating within the group and find an outsider. They pull out the classifieds and points out Mary Resnick, a City Supervisor. He doesn’t care. Meanwhile, Sara goes into the bar and tells Ben that she is in danger with losing Matt. Ben says that it is because she is reserved and is a corpse while having sex. He tells that his night wasn’t good either and says that they were going to get “busy”, but says that Colleen blocked that idea too. Sara says that he needs to act like he doesn’t want her until she asks what the matter is. That is when he needs to go for it. Ben and Sara agree as to what they have to do tonight. Later, Aaron goes out to his Jacuzzi to find Fitz in with Mary Resnick, the woman from the classified. On Ben’s date, he is acting the part of not being interested. Meanwhile, Sarah goes up to Matt and tells that she enjoyed her time with him and would love to do it again. Aaron goes on the date that he organized with Riley, but finds that Riley has a date already.
Later, Sara is trying to act more sexual in her movements and it is clear that it is making Matt uncomfortable. On Ben’s side, Colleen asks if she did anything wrong and he goes in for the kiss. She gets up and says that she is going to “powder her nose” She says that she has a good idea for the next time she is in Chicago. Frustrated, Ben texts Sara and says that he needs help. She texts back to give Colleen an intense message. Ben reads it and agrees. However, Sara realizes her mistake and says that she wanted to text “intense massage”. Ben gets up and yells at the door and tells Colleen to stop teasing him. She opens the door dressed in a piece of lingerie and says that she was going to say that they could have sex, but now it is not going to happen. Sara does her part being “passionate” and Matt says that she is crazy. Matt says that he got weird because she is the first person he has slept with since his wife. She tells that she thought it was her and says that Ben says that she is reserved in bed. Matt asks how Ben knows that and she tells that she used to sleep with him and says that they put that on pause. Matt asks if he can be her friend who she sleeps with, but Sara says that Matt is boyfriend material. However, Matt says that he has to go and says that he’ll see her “around”.
Back at the bar, Aaron says that he thought this was going to be just him and her. Riley says that she thought that Aaron said a group dinner. She feels bad and she says that Aaron doesn’t want to be with her because she is messy and she has a lot of parking tickets and can’t cook. She says that guys hit on her and she sleeps with them. Riley’s date comes back and has his sister with him. Aaron introduces himself. The episode ends with Sara and Ben talking about their night and Sara asks if their “thing” is getting in the way of them meeting someone really special. Matt laughs it off and says no. Sara finds the Radicchio. The next night they go to the bar and Mary Resnick comes in and asks if Fitz has been using her name to get people out of parking tickets. He says that he has and she smacks him. He tells his friends that she is going to be Mayor one day.