When Dee Dee befriends Spencer, Mona becomes concerned that her sister is stealing her best friend. Meanwhile, Mona leads Dee Dee and Spencer into believing she is still dating Brian the exterminator even though he hasn't call her after their very hot date.

Mona fears a lonely Valentine's Day, but her tears may be for naught when two men from her (recent) past both ask her on dates. Also, Dee Dee is miffed that Neil would choose work over her. Meanwhile, Big Dee Dee is angry with her husband, who also chooses work over her.

Dee Dee and Big Dee Dee plan a ""surprise"" party for Charles and Big Dee Dee's 24th wedding anniversary. While putting together a slide show, Dee Dee discovers that there are very few photographs of Mona with their father. She feels sorry for her sister and makes several attempts to cheer her up (first creating fake photos of the two, then trying to set up a lunch date for Mona and Charles), but only angers her further. Mona explains that she had accepted the fact that she and her father didn't have the closest relationship, but Dee Dee is inadvertently opening the wounds. Phyllis produces evidence that proves Charles wasn't quite as distant as it seems. Spencer develops an attraction to Camille, a photographer working with Delicious Records artists. Adam constantly tries to alert Mona about Spencer's feelings for her. He finally tells her the truth, but they discover that Spencer is involved with Camille. Meanwhile, Dee Dee becomes annoyed when her ""summer fling"" starts to get

Dee Dee takes a pregnancy test, although Mona feels that she might be overreacting (her period is only a day late). Before Dee Dee can check the results, her mother bursts and demands to use the bathroom. Big Dee Dee also takes a pregnancy test, which turns out to be positive. She is startled, but she and Charles quickly accept the news. Big Dee Dee gets to rub her pregnancy in the face of Phyllis, who had believed Big Dee Dee was going through menopause. Mona is upset to realize that Spencer has been seeing Camille for some time, but hadn't confided in her. He claims that he wanted to keep quiet until he knew the relationship could last. Phyllis chastises Mona for letting ""her"" man get away, while Adam refuses to believe that Spencer is over Mona. He insists that he is happy with Camille, adding that Mona would never want him anyway. Mona patches things up with Spencer and says that she is very happy for him.

Camille returns from a vacation in London and behaves coldly toward Spencer. She finally admits that she is desperately homesick and has decided to move back to England. Phyllis upsets Mona by giving her a gift, a cat she saved from a shelter. (She sees it as a sign that Phyllis has given up on Mona ever giving her grandchildren.) Big Dee Dee decides to record a song as a birth announcement. Mona helps Dee Dee and Big Dee Dee search for an affordable studio. Mona meets Nick, the charming and handsome producer who runs one of the studios. They immediately hit it off and make a date. She has to cancel to tend to Spencer, but Nick is understanding, and later shows up with food. Dee Dee counsels Spencer and encourages him to tell Camille his feelings. He is devastated to find that she was about to leave without saying goodbye. She says that she enjoyed their relationship, but that it moved too quickly for her. Mona doesn't have enough time to look after the cat, so she gives it

Mona and Dee Dee agree to get each other dates as a birthday present. Dee Dee does some thorough research and finds Mona a seemingly perfect guy, James, and the two get along well enough to set up a second date. Mona waits until the last minute to begin her search and is forced to turn to a less-than-helpful Spencer and Adam as she tries desperately to track down someone for her sister. Meanwhile, Dee Dee convinces a reluctant Big Dee Dee to let Mona and Phyllis join them for a mother/daughter portrait sitting. Big Dee Dee and Phyllis see the photograph as another opportunity to outdo each other and go all out to find the flashiest outfits possible.

Mona panics when a screw-up by Spencer may cost Delicious a chance to have mega-successful producers Jimmy Jam and Terry Lewis help judge a showcase with the talent search finalists. Meanwhile, Dee Dee tries to prove to Mona that she can get by without their father's assistance after she gets downsized from her new job before her first day.

Mona grows very nervous about her role in selecting the Fast Track winner, especially after Kai decides to step aside and leave the decision about whom Delicious will sign to Mona. Dee Dee urges Mona to have confidence in her abilities. After a workshop, studio session and live showcase, Mona, Jimmy Jam and Terry Lewis select the winning act.

Mona decides to embrace her birthday for a change and throw a party honoring Dee Dee and her. However, the event is spoiled by Phylllis's gift to Mona: a certificate to have her eggs frozen at a fertility clinic. Meanwhile, Dee Dee receives a great job offer with a law firm, but decides to pass because her instincts tell her something else will come along. Her friendship with an NBA star soon leads to a new opportunity for a career.

Dee Dee begins work as a sports agent, but clashes with a cocky co-worker. They are both upset when their boss forces them to work together to bring in a hot football player. Meanwhile, Adam recommends that Mona and Spencer follow his lead by signing up for an online dating service. They decide to write each other's profiles after having difficulty completing them on their own.

Mona fears that Chase hasn't made any special plans for Valentine's Day, so she tries to take action. Dee Dee sets Brett up on a blind date in the hopes of curing him of his bad mood concerning the holiday, which stems from a broken engagement. Spencer gets close with a rival music executive whom Mona despises. Adam grows irritated with his Valentine's date, a man with whom he's shared a yearly tryst for the past 10 years.