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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'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.
Inspired by their friends at a party, Jamie and Fancy try a role-reversal exercise that leads to a late-night argument about their future together.
Jamie is looking forward to a visit from his mom, a chanteuse whose maternal duties often took a back seat to her career. The opposing coach, who is an NBA player is sure to beat Jamie, unless Jamie can find some help.
Jamie and Fancy then privately fantasize about each other.
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.
Attempting to ignore the condescending hotel accountant, Braxton P.
Hartnabrig, and the dumb bellman Dennis, Jamie vies for the attention of the sexy and shrewd front desk clerk Francesca "Fancy" Monroe.