Set on the south side of Chicago, How U Like Me Now? is a comedy that captures the lifestyles of several twenty-something African Americans. Centering on a slacker named Thomas (Darnell Williams) and his ambitious girlfriend Valerie (Sally Richardson), the film follows the couple as they decide whether to continue their relationship or call it quits.

When Stedman Austin, a high-powered promoter, organizes a "Perfect Model" contest, Mario starts trouble by entering his socially unrefined girlfriend Linda.