Plot
Party boy Bobby still lives at home and is a low-level mail clerk in a big real estate investment firm. He has been there for two years but aspires to enter the trainee broker program. Bobby feels especially frustrated because a guy with less time in the mailroom gets in first.
Waymon Tinsdale is an uptight African-American in middle management at the firm on the verge of making partner. He is at lunch with a senior partner when he sees beautiful party girl Natalie, a hostess there and is instantly interested but tongue-tied.
When Waymon returns to his office he finds Bobby having fast food at his desk, hitting on a woman on his phone. They fight over the trainee program, Wayman pointing out he has less prestigious qualifications and dresses too informally.
Seeing the headshot of Natalie that Waymon has from helping her earlier, Bobby tells him he has no chance. They make a deal in which Waymon will try to move Bobby to the trainee broker program if he helps him meet her.
After an unsatisfying date night with Deidre, Waymon meets Bobby at a club. He's unsuccessful in meeting Natalie. Waymon returns to the office to continue on a report due the next day. His secretary wakes him to find out he's late to a meeting. The partner is livid that the financial report is still not complete, so he promises to have it complete for Friday.
Bobby convinces Waymon to buy some more hip clothes. They then go out to a bar where Natalie is a cocktail waitress. This time she notices him. Waymon spends the whole of Thursday on the report, which he plans to send first thing in the morning.
At a cocktail party, Waymon tells David who's also vying for partner that he completed the Savoy tower report. Deidre responds very negatively to Bobby's arrival, threatening to dump Waymon if he leaves with him. The guys head to Natalie's work, only to find out it's been closed down by the IRS. Waymon takes her off, she tells him of her dream to be a club owner and they spend the evening together.
Meanwhile, David and his trainee sneak into the office and make changes to the report. Bobby gets it to the potential Japanese investors, who pull their bid. Waymon, thinking Bobby screwed up, gets him fired. He himself is told that if he doesn't get another buyer by Monday he is also fired.
Natalie shows up in the office for her lunch date with Waymon admidst his stressful search for a new investor. He's cold and upsets her, so she tells him off and leaves. Then his secretary comes, showing him that Bobby couldn't have been to blame. Waymon seeks him out, apologizes and tells him about their need for a big investor. Bobby says to have his big presentation set for Monday and goes.
First thing Monday the Holleran brother of the Harlem National Bank arrive, and Waymon realises he'd met them out with Bobby in a club. After his presentation they sign on as the Tower's investors, and Waymon is made partner. In the lobby when they find David his trainee rats him out and he gets fired.
Waymon begs Natalie for forgiveness, and after he and Bobby take her to a huge space. The Holleran Brothers offer to invest in her club, sharing the profits 50-50
