- Robert goes out on a first date with Debra's friend Amy, and Raymond suddenly become insecure about his looks when everybody starts saying that Robert is more handsome than him.
- As the episode begins, Debra has her old friend Amy over to the house. As they talk, Robert walks in asking for donations for the police department. Debra ends up introducing Robert and Amy. After a short talk, they plan a date. Later, Robert wants to break it off because he becomes self-conscious of his looks. He even calls himself the Hulk, to which Ray replies that he's not green. While Ray makes jokes, Debra tries to boost Robert's confidence by telling him how handsome he is. But she stops short when she's about to say that Robert's the best-looking of the Barone men. While Ray is shocked, Robert exits with a smile and a whole ton of confidence. Ray has a discussion with his parents about his and Robert's looks, and they end up saying that Robert was the better-looking son while Ray was the sweetest and nicest. Robert returns having had a wonderful time with Amy, and Ray comes back with a tan, gelled hair and new clean clothes. Debra laughs and comments that he looks like George Hamilton. She explains that Robert is good-looking, but it's Ray that she's attracted to.
- When Debra's friend Amy (Monica Horan) contributes to Robert's Police Welfare Fund, she and Robert hit it off. Amy is a successful professional with a corner office but is not having much success with the dating scene. Amy and Debra used to work together at the same office. But then Debra decided to have a family and Amy went the career route. Robert had come to ask for a donation from Debra, but Amy is excited to know that Robert is Ray's brother and starts chatting him up. Robert even eats the cookie dough straight from the packaging, just like Amy does.
Ray is clear that Robert is not ready for a relationship, while Debra says that it's been a year since his wife left him. It is time for Robert to move on with his life. Robert's wife left him for a guy he arrested. Amy asks Robert out on a date. When Robert is unsure about going on a date (Because of the ugly divorce with his first wife), Debra mentions that he is the most handsome Barone she has met. Robert calls himself the Hulk. Ray is full of advice for Robert, like not to push Amy's head in when he opens the car door for her, like he would do to a criminal he is arresting.
Meanwhile Ray continues to undermine Robert's confidence by saying that he still can't believe that a woman like Amy would ask him out voluntarily. Ray becomes very insecure about this comment and becomes obsessed with his appearance. Like his bottom teeth and the large pores on his large nose. Ray believes that if Debra had to do it all over again, she would probably marry Robert. Debra makes it worse when she says that Ray has a large nose.
Robert begins dating Amy. When Marie agrees with Debra, that Robert is the handsome one in the family and Ray is the adorable one. Robert used to have an old-fashioned movie star type look. Frank is offended as Ray looks like him. But even Frank agrees that Robert is the looker in the family. Meanwhile Robert is insecure when Marie says that Ray is the kindest and the sweetest boy in the world. The kind that every mother hopes for. Ray gets a spray-on tan and a new hairstyle. He also spends a lot of money on beauty and hair products (like hair gel, hair mousse, hair Volumizer, deep pore cleanser, clarifying lotion) and Debra is tickled by his insecurity. Debra cannot stop laughing at Ray when he steps into his house. Debra says that Robert is handsome, but he is not the one she is attracted to. Debra shares a dance with Ray to make him feel better. Ray gives all the grooming products to Robert.
Note: In this episode it is mentioned for the first time that Robert is divorced for a year and his wife left him for a man he arrested. Later, in the episode "Robert's Divorce", it is shown that Marie threw his wife out of the house because of her behavior towards Robert. This is also the first appearance of Amy.
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