Tim, Eddie, and Malcolm watch the Chief's game at the apartment and talk about Eddie playing football in high school.
At McGee's, Malcolm tells Eddie he's worried about Nicolette. Eddie says he doesn't see it, but then Nicolette sighs and says, "This is the worst day of my whole life." They walk over to the table and ask her what's wrong. She tells them that she is having a problem with her boyfriend, Lt. Stanley Proctor. She says that things are going great, but she knows he wants to ask her to marry him, but he can't seem to get the words out. She asks them to help her make Stanley more confident like they are, but not as obnoxious. They agree, and she thanks them.
Malcolm, Eddie, and Stanley talk at the apartment. Malcolm asks him what his intentions with Nicolette are and he tells them that he has been thinking about proposing to her, but can never get the words out. Eddie offers to pretend to be Nicolette and let Stanley practice. He does, but still can't get the word "marry" out. Malcolm suggests if he can't say the word, then he isn't ready for it, but he disagrees, and swears he is.
At McGee's, Malcolm tells Tim about Nicolette and Stanley's situation. Stanley walks in and Eddie greets him. He asks him and Malcolm what they wanted and they say that they wanted him to spend some time away from Nicolette. They point out two women who they say are checking him out, and send him over there. Stanley walks over and Eddie tells Tim that the women are actually Malcolm's waitresses, who have the day off, with pay, to act interested in everything Stanley does, part of their plan to boost his confidence.
Later on, Stanley is sitting at the bar and Eddie yell "What!?" Stanley tells him and Malcolm that for the first time in his life he got to be smooth, and he isn't ready to be tied down now. Malcolm and Eddie call over one of the waitresses, Cidnee, to explain that it was all an act, but she says it was only an act at first, and after she learned how nice he was, she liked him for real. Stanley says they should tell Nicolette, because it'd be better from friends, and then he leaves to go on a date with Cidnee. On there way out Malcolm tells Cidnee that she's fired.
At the apartment, Nicolette knocks on the door and tells Malcolm and Eddie to let her in. Eddie tries to go to bed, but Malcolm tells him that since they both let Nicolette down, they both have to tell her. She comes in and tells them that she's pretty sure Stanley will ask her tonight, then tells them that maybe she will name her first to children Malcolm and Eddie. Eddie tells her that they have to tell her something and then Malcolm begins explaining what happened. She gets upset and they try to calm her down. She tells them if she doesn't have romance, neither will they, and then leaves.
Later, at McGee's, Malcolm tells Nicolette that she got her a fake date for the night to make Stanley jealous. Then, Eddie walks in, dressed in a suit, and hands Nicolette flowers. Stanley walks in and gives Malcolm a screw driver (which Malcolm called and asked to bring over immediately off screen). Stanley and Malcolm go to the bar, while Eddie and Nicolette dance and act like they are having a wonderful time. Stanley can't take his eyes off of them, and barely listens to anything Malcolm tells him. Malcolm tells Stanley to fight for Nicolette if he wants her. Stanley walks over to her, gets on his knee, and asks her to be his wife. She says she has been dreaming about that moment for months, but then tells him no. She tells him that she does love him, but the past couple of days have showed her that he isn't ready for that kind of commitment, and she may not be either. He says this makes him love her even more, and she says she doesn't blame him, but then tells him good-bye.