Dwayne is under a lot of stress after being so over occupied while Juleesa starts her own business from home after not finding a suitable place elsewhere.
Dwayne and Whitley's parents both come together for their engagement party. When both mothers get into a heated exchange Dwayne and Whitley are going to an exchange as well when Dwayne gets cold feet but it is Whitley who calls off the engagement
Whitley throws herself into an art exhibit in order to forget her break-up with Dwayne, and Kim is furious that Whitley wants to include stereotypical "Mammy" items in the exhibit. Whitley discovers an unpleasant truth about one of her ancestors.
Whitley and Dwayne struggle with their first holiday apart. The Taylor Family is having a conflict of interest over Christmas traditions. Therapist, Dr. Langhorne advises everyone to holiday cheer.
Dwayne becomes frustrated with Ron's inability to pay his fair share; Whitley, Kim and Lena intervene when they see Freddie losing herself in her relationship with Shazza.
At a hotly contested Hillman-Virginia A&M game, Ron accepts a sucker bet from three white A&M students, then gets into a fight with them when one of them starts to spray a racial epithet on his car in revenge. In a cell, the men proceed to give very different accounts, mediated by a white officer who challenges both groups' assumptions.
Freddie's pen pal, Jamal, is an ex-con and he visits Hillman, where Whitley is drawn to him. Ron and Dwayne get involved and find an expensive camera and other items in Jamal's belongings and accuse him of stealing.
When Whitley is promoted at work, she is faced with sexual harassment by her new boss. Colonel Taylor is thrilled to learn Terrence has finally chosen a career, until he finds out it's dance.
Byron Douglas is impressed with Whitley's fund raising skills and asks her to help with his Senate campaign. Mr. Gaines has troubles with the lease at The Pit and Byron gets involved.
Whitley and Byron are getting serious, but Whitley still has feelings for Dwayne. They end up sleeping together when Dwayne arrives at Whitley's place to discuss their relationship. Kim finally goes out with Ron to a club but ends up leaving when every woman seems to have a past with Ron.
Lena is losing her engineering scholarship until she writes a moving story about her father, which later is proven to be fabricated. It earns her a journalism scholarship and brings her closer to her gambler father. Whitley jeopardizes Byron's fund raising when she wears a fur to an event.
Byron's opponent brings details of a stripper in Byron's past to light but Byron refuses to fight back, and just wants to discuss the issues. Byron wins the election and proposes to Whitley which upsets Dwayne. Jaleesa gives birth with the help of Kim and Freddie.