Bullethead looks on while Romeo charms a classmate, Tomika, into accepting a date for Saturday night. Bullethead criticizes his style, saying he can do better. As Bullethead approaches a beautiful blonde, Steve and Romeo watch him in action. Bullethead is also successful in winning the attentions of the young woman.
Cedric is not happy to learn Steve's mother will be visiting because she does not like him. Steve reminds him he killed Mother Hightower's dog, Mr. Peanut, and despite the fact it was an accident, she has good reason to dislike Cedric. On the other hand, Regina is thrilled to hear about the visit, as she was always fond of Steve's mother. Steve invites her to stop by the apartment to say hello. While Cedric hopes Mother Hightower is willing to let bygones be bygones, he immediately discovers she still holds a grudge when she demands the "dog-killer" give up his room and sleep on the sofa during her stay. Mother Hightower does not wait long before beginning her criticism of Steve - starting with why he isn't married yet.
Back at school, Sara and Sophia tell Steve they just got new jobs at a '70s restaurant, Superfly, where a menu item is named after Steve - a grilled cheese sandwich on white bread. Meanwhile, as Bullethead and Romeo plan their Saturday night double date, a second girl, Angel, asks Romeo for a date Saturday and he accepts. He plans to meet both girls at Superfly - Tomika from 7-9PM and Angel from 9:30 on.
When Mother Hightower invites Ruth Anne, a date for Steve, to dinner, Steve tries to squirm out of the situation. He tells Mother Hightower he can't date the woman because he is already involved with someone. When Regina arrives for a visit, Steve quickly decides to pretend Regina is his girlfriend. Leaving his mother and Ruth Anne with Cedric, Steve takes Regina aside to explain his predicament. As Regina goes along with the ruse, Cedric makes his move on Ruth Anne. Uncomfortable, Ruth Anne leaves…with Cedric close behind.
The next day, Steve talks Regina into helping Steve out one more time by joining him and Mother Hightower for dinner at Superfly. However, at the restaurant, Steve must then explain to Sara and Sophia why he's out with their principal just as Bullethead and Romeo arrive with their dates, too. When Romeo's dinner with Tomika runs late and Angel arrives early, Romeo finds a growing problem on his hands. He enlists Bullethead in an effort to keep his two dates from discovering one another. Regina also gets some intimate family history Steve would have just as soon kept hidden. However, when Mother Hightower offers her a valuable family heirloom, Regina insists Steve admit to their deception. Angry about the lies, she and Regina leave. Romeo's dates eventually find out about each other and also leave.
Back at the apartment, Mother Hightower asks Cedric for a ride to the airport. He is more than happy to oblige, thinking she might now like him. She tells him she still doesn't, but really wanted to make Steve feel bad. Finally, Steve tells Mother Hightower the truth: she must trust that she raised him correctly and can't control his life anymore.