Aspiring politician Ron Brown shows up at Mona's door in search of votes, and takes a liking to her. Phyllis quickly pushes him to ask her out, and they agree to a date. Mona then learns that Big Dee Dee recently arranged a date for Dee Dee and Ron, who have been friends since childhood. The sisters are unsure about dating the same man, but their mothers insist that it will be all right (as it is unlikely that both will be compatible with Ron). Phyllis and Big Dee Dee treat the whole thing as a personal competition. Mona and Dee Dee like Ron, but decide that he isn't worth the potential damage to their relationship. They agree to do the ""mature"" thing and stop dating Ron, but each keeps seeing him behind the other's back.

Camille sets up Mona on a date with her best friend, the handsome and engaging Carlo, whom she hasn't seen for years. Mona is thrilled when she and Carlo hit it off, and believes he might be a long-term boyfriend prospect. However, Carlo is actually in love with Camille and wants to pursue a relationship with her. Meanwhile, Dee Dee and Big Dee Dee are desperate to find out the sex of the baby, while Charles insists that they should wait until the birth. The women try to go behind his back to the doctor.

Nick tells Mona that his parents are coming to town for the weekend, and that he would like her to meet them. Mona is very nervous, as she has never met the parents of any of her boyfriends. Nick's parents are decidedly less than thrilled by the fact that their son is dating another black woman. Mona cannot understand why they dislike her, and asks Dee Dee to help win them over. Dee Dee suspects that they are racist, and they overhear the couple making remarks that prove this. Dee Dee recommends that Mona discuss the situation with Nick. However, before she can bring up the subject, Nick proposes. Mona immediately accepts. Phyllis, Dee Dee and a jealous Spencer pretend to be happy for her, but are actually worried. Dee Dee tells Mona that she cannot just ignore the attitude of Nick's parents. Mona admits that she got caught up in the moment and isn't ready to marry Nick. She wants to go on dating; but when he cannot get any reassurance that she might want to marry him one da

Dee Dee makes a date with her favorite author after meeting him at a book signing. All appears to be going well, but Dee Dee reconsiders the relationship after learning that Carter has full custody of his two young daughters. Meanwhile, Phyllis begins snapping at everyone and seeks refuge at Mona's apartment after disagreeing with Ray's decision to take on another shift at the radio station.

After Dee Dee bests her at an online word game, Mona grows frustrated by the fact that she always loses to her sister. She becomes determined to beat her at something, and sees her opportunity when Dee Dee organizes a poker party for one of her law school professors. Their mothers decide to crash the event, where Phyllis winds up winning Big Dee Dee's wedding ring in the pot. Meanwhile, Adam tries to get access to a copy of Spencer's personal music playlist.

Dee Dee tricks Mona into joining her at a singles weekend at an exclusive new hotel. Mona meets a handsome bartender, but Dee Dee repeatedly tries to steer her away from him, claiming that she has her best interests in mind. Spencer and Adam also attend the event, thanks to Adam's successful friend. Spencer enjoys the perks of hanging out with Adam and his friends, but is surprised to discover that people believe he is also gay. Meanwhile, Big Dee Dee convinces Phyllis that her presence in the building and relationship with Glen are driving Mona away.

Spencer continues to shower Naomi with affection after she reveals her HIV-positive status. However, her newfound confidence prompts her to dump him and seek to profess her love for another man. Mona tries to comfort Spencer, but he rejects her for failing to back him throughout the relationship. Dee Dee agrees to join her new actor boyfriend in a reality show, and winds up humiliated. Charles is surprisingly supportive when Big Dee Dee is asked to do a nude scene in her film debut.