J.T. unexpectedly agrees to Shelly's offer to pay for dinner, not knowing that she doesn't have enough money to actually pick up the tab. Shelly asks Rita for help, but she gets sidetracked by an encounter with supermodel Kylie Bax. Meanwhile, Nick borrows from Donovan's wardrobe in an attempt to become more attractive to women.
J.T. and Shelly are all set to celebrate their three-month anniversary with a romantic weekend getaway until J.T. realizes he's already committed to play in a basketball tournament with his friends, and despite his attempt to soften the blow of canceling the trip with dinner and gifts, he still lands in the doghouse. L.A. Laker Derek Fisher guest stars.
On Valentine's Day, the friends debate whether or not it was fate that Shelly and J.T. became acquainted. In a series of flashbacks to six months earlier, J.T. almost meets Shelly in line at a coffeehouse but becomes frustrated by her lengthy order. He also nearly encounters her at DivaStyle, but leaves after getting frightened by the sight of a wedding veil. Meanwhile, also in flashbacks, Shelly comes close to being seduced by handsome cheater Kevin Thorpe , with whom she had broken up. But at the last minute, she asserts her independence, leaves him and puts on the sexy dress to finally meet J.T.—and her destiny—at Z Lounge.
Janie discovers Marty's secret porn stash, and fearing there's a problem in her marriage, sets about trying to remedy the problem with help from Shelly and Rita. Also, J.T. has made a new friend in Cedric the Entertainer, but when this new friend never, ever leaves his side, he becomes an annoyance that J.T. wonders how to ""break up"" with.
Shelly's childhood friend, April, reappears in her life, and her party-crashing antics begin to influence Shelly's behavior, which causes friction between Shelly and her friends Rita and Janie. Meanwhile, Nick receives an email of a dancing stripper and tries to delete it before his boss can see it.
Shelly convinces J.T. to visit her very popular hairstylist Coleman, but when J.T. voices his dissatisfaction with the haircut, Coleman bans both of them from his salon. Shelly begs J.T. to apologize. Meanwhile, when Nick flirts with beautiful delivery woman Danni, a jealous Rita attempts to prove to Nick that Danni may actually find Rita the more attractive package.
Shelly jumps into J.T.'s bar brawl and, with one punch, puts an end to the fight before it even really starts, causing J.T. to feel his masculinity has been undermined. Meanwhile, Donovan breaks up with his latest girlfriend and cons his friends into thinking she dumped him so he can get as much sympathy as possible from his pals.
After her car accidentally catches on fire, Shelly asks J.T. to lend her money for a down payment on a new one, but when he refuses, it causes her to question their relationship. Meanwhile, stuck with an extra ticket to a charity ball, Rita asks Donovan to escort her to the event, and the two friends share a surprising kiss at the end of the evening.
A humiliated J.T. admits to Shelly that he doubts she's the type of girl he could marry after he and his parents see Shelly and her girlfriends drunk and topless in a new commercial for a racy reality video. For her behavior in the video, Janie's husband Marty forbids her to go out. Donovan and Rita valiantly attempt to not discuss their recent kiss. And Nick's appalled that his new girlfriend Dani has an ex-lover's name tattooed on her. )Part 1 of 2)
In an attempt to mend their rocky relationship, J.T. and Shelly sit down for an honest conversation about the effort and compromises each must make if they're going to stay together, but just when she thinks they're making progress, Shelly is shocked to learn that J.T.'s idea of compromise involves her changing her lifestyle. Meanwhile, Nick tries to pretend that he is happy about Donovan's romantic interest in Rita after learning of their newfound mutual attraction.
It's very hard for Shelley to get over her breakup relationship with J.T. So she gets help from a first ever book called ""Self Helpful"" which makes her feel independant while Rita and Janie worry that Shelley is still upset inside. Meanwhile J.T. can't get over the breakup relationship with Shelley and decides to let Nick and Donovan help him get over the breakup.
Shelly wants her things that she left at J. T.'s apartment. When she uses email to ask for them back, he responds he wants the money he ‘loaned' her to buy a car. Shelly decides to get the things from the apartment with the help of Rita and Janie. While there, Shelly decides to take the things she gave J. T. as gifts. After the police get involved, Rita and Donavon see the ugly side of the breakup, they decide to remain friends.
Shelly hurts her knee when working out with Rita. J.T. has fixed the problem before so Janie and Rita urge Shelly to go see him. She finally gives in and meets a handsome doctor who asks her out. J.T. is not happy about the date and sets out to wreck it. Donovan bets a bragging Nick that he cannot run the bar for one night.
Shelley breaks the ""no dates"" rule and invites her new boyfriend to the New Year's Eve party, and everyone swaps stories about past dates. Everyone discusses their worst New Year's Eve dates ever! Whoever had the worse one got an entire bottle of champagne. Rita's date: died on New Year's Eve of a heart attack after she showed herself nude to him. Nick's date: a ventriloquist dummie. JT's date: believed that she was ""Wonder Woman"" Janie & Marty's first New Year's Eve in their new house was ruined by the surprise visit by Marty's mother. Donovan's date hooked up with an old boyfriend during her date with Donovan. Shelley found out that Mark was once gay and proposed to his ex-boyfriend on the top of a mountain.
When Grant (guest star Sharif Atkins) tells Shelly he’s had an HIV test because he’s ready to take their relationship to the next level, it sparks the whole gang to go get tested. Golden Brooks (UPN's GIRLFRIENDS) guest stars as Nurse LaDonna and Marteniz Brown, a HIV/AIDS educator from Detroit, guest stars as Roderick, a clinic counselor. Donovan's request for residency into the United States is denied; he is informed that he must leave the country within 30 days. JT realizes that he's still in love with Shelly.
When Coleman's (guest star Phil LaMarr) hair salon gets shut down, Shelly and the girls help set him up in their shop temporarily, but they soon regret the decision when the demanding stylist takes over DivaStyle. Meanwhile, the gang learns some surprising information about Donovan after an immigration raid on Z Lounge.
After spotting Janie helping Grant (guest star Sharif Atkins) shop for an engagement ring, a distraught J.T. turns to Rita and his parents for advice, which leads to a dramatic showdown between the two men at Shelly's birthday party. Meanwhile, wanting to avoid tearful goodbyes as he leaves for England, Donovan sneaks out of the party and mulls over his future plans in the cab to the airport with driver Rufus (guest star Ludacris).
A night of grazing on junk food leads the gang to realize they can each stand to lose some weight, but Shelly cheats on her diet, and crosses the line when she can't fit into her clothes. Also, the diet agreement is put in danger when Janie enlists the gang to help her prepare for her church bake sale.
While spending Christmas at her mother's, Shelly wants to deck more than the halls when one of her mom's students, who's also staying there, replaces Shelly as the center of attention. J.T., Donovan and Nick decide to watch football instead of celebrating the holidays, but soon they come to a conclusion how much they miss the tradition
Shelly finds out that Janie's baby brother Paul still has a crush on her after all this time, but she doesn't know how to handle the situation now that Paul is an adult. Nick embarrasses the gang at Janie's church when he accidentally drops a $100 bill in the collection plate and then attempts to either get it back or at least, get his change
Shelly's mother Beverly finally admits to Yusef, Shelly's father, that she is carrying his child, and Shelly questions Yusef's ability to be a father again. Meanwhile, Janie finds out that Rita is having Botox parties after hours at DivsStyle. Nick is caught in a love triangle when Lynn tries to break it off with her husband, Jamal