Regina agrees to date the "man-boy" who services the office water cooler. - - - As Regina is nursing an infatuation with, Dexter, the young man who delivers their water, Steve prides himself on his relationship with cardiologist Dr. Glenda Burke. When Bullethead and Romeo accidentally destroy his autographed copy of "ROOTS", Steve is irate. Lovita encourages Regina to pursue a date with Dexter. And when Dexter expresses an interest in Regina, Lydia makes it clear she too has a crush on him. Meanwhile, when Lovita enrolls in an art class, Cedric is stunned by her horrendous first project but hangs it in the living room. Steve decides to punish Romeo and Bullethead by transferring them out of his class. After agreeing to a dinner date with Dexter, Regina allows Lovita to help her find a younger look. But once Dexter announces they are going on a double date with his mom, Regina is stunned to learn the other couple is none other than Steve and Dr. Burke. Seeing her son is dating an o