Strictly Business (1991)

Waymon has a great job in real estate and a promising future but hes also trapped in a loveless longterm relationship He meets Natalie a beautiful clubhopping hipster and quickly falls in love Realizing hes just not cool enough to attract her on his own he seeks the help of his friend Bobby a freespirited smooth talker who works in the mail room at Waymons firm and utilizes the predicament as leverage to advance in the company