Doug Ireland (Michael J. Fox) is an enterprising young hotel concierge who goes to great lengths to satisfy the guests and appease the eccentric staff members at New York City's declining Bradbury Hotel. Although his charms often earn him generous $100 tips from customers, his romantic advances are rebuffed by Andy Hart (Gabrielle Anwar), a young saleswoman at the hotel's perfume counter who claims to be in a relationship with a wealthy, married man.One day, an acquaintance gets Doug a meeting with billionaire mogul Christian Hanover (Anthony Higgins) when he comes to the Bradbury to meet his mistress. Doug proposes his life-long dream to build his own hotel on Roosevelt Island after saving years of tips to take out an option on the property and hopefully move out of his cramped one-room apartment. Christian is impressed by Doug's business plan, and agrees to consider making a $3 million investment. When Christian's mistress arrives, however, Doug is surprised and hurt to find Andy standing at the door. Once Christian leaves, Doug accuses Andy of being superficial, but she insists the billionaire plans to divorce his wife for her.The next day, Internal Revenue Service (IRS) Agent Ed Drinkwater (Bob Balaban) informs Doug that he is under investigation for failing to report his full income to the tax bureau by using his tips on the Roosevelt Island property venture. Keen to move forward with the hotel, Christian Hanover asks Doug to return the favor by attending one of Andy's singing performances in his place.At the club, Doug apologizes for his earlier behavior and lies to Andy about Christian's whereabouts, hoping to quell her suspicion that he has returned to his wife in the countryside. The next day, Christian telephones Doug claiming Andy is on her way to visit him under the false impression that he is alone.Using his business connections, Doug hires a helicopter to fly to Southampton, New York, in time to stop Andy from running into Christian's wife at the Hanovers' Memorial Day party. He locks Andy in a bedroom while dodging Mr. Drinkwater, who arrived at the house trailing Doug. Inside the room, Andy befriends one of Christian's famous protégés, fashion designer Julian Russell (Isaac Mizrahi), before Doug takes her back to the city. At Andy's apartment, Doug goes upstairs to use her bathroom and Andy packs a bag to leave town. When Christian telephones, Andy refuses to speak to him, but Doug convinces them both to reconcile.The next day, Christian once again asks Doug to keep Andy company while he is detained at work. Although he initially refuses, he remembers Christian's commitment to the hotel investment and agrees to spend the day taking her about town. When Andy asks Doug why he is so beholden to Christian, he takes her to Roosevelt Island to show her the property he hopes to develop.That evening, Doug drives Andy to her date with Christian. On his way home, however, he sees Christian dining with another woman in a restaurant and returns to have a drink with Andy, not mentioning what he saw. While they wait, Andy dances with Harry Wegman (Michael Tucker), a Bradbury guest whose twenty-year marriage Doug has helped revive. Although Andy assumes Doug expected something from him in return, Mr. Wegman insists Doug's actions were selfless. Doug and Andy nearly kiss, but are interrupted by the maitre d' informing them that Christian has called, asking to meet Andy at their usual Bradbury suite.Back at the hotel, Andy denies any romantic possibility between her and Doug and belittles him for playing the role of Christian's "houseboy." Christian announces he has resolved the issue with the IRS and decided to begin construction on Doug's hotel. On his way out, Doug overhears Christian tell Andy he has finally left his wife.During Julian Russell's fashion show later that week, Christian gives Doug the property paperwork, which will transfer the lease agreement to the control of his corporation and end Mr. Drinkwater's audit. Doug mentions Christian's divorce, but the billionaire insists his wife has allowed him to continue having affairs if he agrees not to end their marriage. Believing Christian is loyal, Andy leaves the fashion show to accompany him on a trip to Italy. As they drive away, Doug tears up the papers and asks his connections to help him create a traffic jam on the Queensboro Bridge. He borrows a horse from a hansom cab driver and rides to catch up with Andy. Meanwhile, Andy learns that Christian conspired with Mr. Drinkwater to trick Doug into relinquishing control of the property rights. Furious, she gets out of the car and walks away, spotting Doug as he runs in her direction across the bridge.Sometime later, Doug and Andy marry, and Doug receives a telephone call from Mr. Wegman, who acquired a copy of Doug's hotel plan from the elderly Bradbury bellhop Milton Glickman (Fyvush Finkel) and agrees to fund the development. In the final shot, Doug and Andy kiss in the lift of the Bradbury .