Shelly, a single young woman, has her perspectives on love and relationships sorted out by a close group of friends. She finds herself attracted to one of those friends, J.T., during a night on the town.
Shelly finds it hard to resist J.T.'s charms, but Janie warns her about keeping a cautious distance after she spots J.T. in a store buying a large box of condoms.
Shelly makes a calculated effort to learn more about J.T., so she rummages through his stuff. Meanwhile, Donovan gives Nick a recommendation for a top tattoo artist.
After Shelly and J.T. attend a party which creates some feelings between the two, both consider the possibility of dating one another exclusively.
Shelly and J.T. take salsa dancing lessons and get an attractive male dance instuctor, only after J.T. decides to quit, Shelly keeps going. Meanwhile, Rita moves into a new apartment.
When Shelly feigns interest in paying for dinner with J.T., he calls her on it and agrees to let her pay. Meanwhile, Nick copies Donovan's fashion sense.
J.T. gets himself on Shelly's bad side when he cancels a romantic three-month anniversary weekend with her due to a basketball game commitment.
Shelly tries to win the repsect of J.T.'s mother after she finds the couple in bed together and disapproves. Meanwhile, Rita breaks up with her man after their sexual role-playing leaves her feeling unempowered.
J.T. feels wounded when Shelly tells her girlfriends the details of their intimate bedroom time, which manages to then be told to rapper Missy Elliott during Janie's party.
The appearance of J.T.'s ex-girlfriend brings out the competitive side in Shelly.
J.T. becomes weary of Shelly's constant absence as she works long hours over the holiday season. Meanwhile, Donovan gets a visit from his former girlfriend.
Nick gets fed up with Shelly's way of dominating the space in the townhouse he shares with J.T. and decides to boot her out, placing J.T. in the middle of a bitter argument between girlfriend and best friend.
Shelly and J.T. look back at the circumstances that led to their first fateful meeting.
Shelly is irked when her sister, Simone, comes to town for a visit and, with her bubbly presence, begins to overshadow Shelly just like when they were kids.
Janie turns to Shelly and Rita for marital advice when she comes upon Marty's hidden porn collection. Meanwhile, J.T. becomes chummy with Cedric the Entertainer, but soon begins to find Cedric more of an annoyance that he has to lose than a friend.
Shelly's college friend comes to town and brings out the wild side in Shelly, but Shelly's partygoing ways cause a spat between her, Janie, and Rita.
J.T.'s behavior gets himself, along with Shelly, cut off as customers by Shelly's hairstylist.
Shelly threatens J.T.'s sense of male machismo when she takes charge of a bar brawl on his behalf.
Shelly gets a legal ambush when she decides she won't work with an artist named Rodney P.
J.T.'s refusal to lend Shelly money causes some conflict within their relationship. Meanwhile, Donovan and Rita find themselves sharing a kiss.
J.T. confesses to Shelly that he's not sure he can marry her after his parents confront him about an appearance they've caught of her in a risque reality video.