How U Like Me Now (1992)

This multi-layered comedy follows a group of young African Americans as they struggle for both financial and sexual fulfillment in early '90s Chicago. At the center are underachiever Thomas and his ambitious yuppie girlfriend Valerie, surrounded by friends and relatives who are full of advice (among other things) on how the couple should deal with their stormy relationship, despite the fact that none of them has a clue.