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Jamie's left in charge for the weekend with one rule — no wild parties — a promise that's hard to keep when the Westside Connection checks in with a wad of cash and a huge entourage.Jamie must compete with a smitten Ice Cube for Fancy's affection.When a call from her agent pulls her away from yet another important night in her son's life, it forces Jamie to face some hard truths about their relationship. When Jamie ignores Fancy in favor of a poker game with the guys, she crashes the game and shows everyone how well she can play.Jamie's bawdy present for Braxton winds up in the hands of Helen (Ellia English), who mistakes it for a gift she's giving a nun. Meanwhile, Braxton has problems with the Y2K upgrade he installed on the hotel's computer system.Meanwhile, due to Junior's negligence and compulsive gambling, the hotel is in serious debt.Junior convinces Jamie to go to a casino and win enough to save the hotel. Unfortunately, when Jamie quits while he's ahead by throwing the dice down, the dealer thinks Jamie wants to continue betting, and Jamie loses everything.Jamie is jealous when Fancy's smooth-talking ex-boyfriend Kenneth sweeps into the hotel flashing plenty of cash—and a diamond ring.However, news from two mysterious guests tells Jamie it's not time to ring those wedding bells just yet: they're about to nab a notorious scam artist.
Hartnabrig, and the dumb bellman Dennis, Jamie vies for the attention of the sexy and shrewd front desk clerk Francesca "Fancy" Monroe.Thrilled, Jamie convinces Charles to stay in the hotel for a few days, then witnesses Charles making romantic advances to Helen.Jamie must choose between advancing his career or standing up for his family.After his credit card is denied while clothes shopping with Fancy and her well-to-do parents, Jamie must prove to her father that he will be able to provide for her.Meanwhile, Braxton is forced to cut the hotel's budget.
Eventually, Jamie annuls the contract by threatening to reveal some embarrassing information about the producer. Jamie takes on the challenge of coaching a Pee-Wee basketball team, but gets frustrated during a game and challenges the opposing coach to a personal grudge match.