Doug Ireland, portrayed by Michael J. Fox, is a resourceful young hotel concierge dedicated to ensuring the satisfaction of guests while managing a quirky staff at the struggling Bradbury Hotel in New York City. His charismatic personality often earns him sizable tips, like the generous $100 he receives when impressing guests. However, his romantic overtures towards Andy Hart, played by Gabrielle Anwar, a captivating saleswoman at the perfume counter, are repeatedly dismissed, as she insists she is in a relationship with a wealthy, married man.
One fateful day, a friend arranges for Doug to meet the billionaire mogul Christian Hanover, skillfully portrayed by Anthony Higgins, who visits the Bradbury to rendezvous with his mistress. During their exchange, Doug excitedly shares his ambitious dream of developing a hotel on Roosevelt Island, having diligently saved up his tips to secure an option on the property, thereby seeking an escape from his cramped one-room apartment. Impressed with Doug's vision, Christian contemplates a significant $3 million investment. Yet, Doug’s excitement turns to disappointment when he discovers that Christian’s mistress is none other than Andy.
After a heated confrontation where Doug accuses Andy of being superficial, she staunchly defends her relationship with Christian, claiming he plans to leave his wife for her. The following day, Doug's life takes a turn when he is confronted by IRS Agent Ed Drinkwater, played by Bob Balaban, who informs him of an investigation due to his failure to report his full income from tips related to the hotel project. Determined to move forward with his hotel aspirations, Doug reluctantly agrees to cover for Christian by attending one of Andy's singing performances.
At the club, Doug seizes the opportunity to apologize to Andy and fabricate a story about Christian’s whereabouts, hoping to alleviate any doubts she may have. Soon after, Christian calls Doug to inform him that Andy is en route, mistakenly believing she is visiting him alone. In a bid to prevent a disastrous encounter at a party hosted by the Hanovers, Doug employs his connections to charter a helicopter to Southampton, New York. Ingeniously, he locks Andy in a bedroom to shield her from crossing paths with Christian’s wife during the Memorial Day festivities. Inside, Andy meets one of Christian's acclaimed protégés, fashion designer Isaac Mizrahi, sparking an unexpected friendship.
Returning from Southampton, Doug takes Andy to her apartment where he hopes to continue their connection. However, tensions rise when Christian calls, and despite Andy's refusal to communicate, Doug manages to mediate their reconciliation. The next day, Christian tasks Doug with keeping Andy company while he’s busy at work. Initially hesitant, Doug remembers Christian’s promise to invest in his hotel and agrees to guide her around the city.
During their excursion, Andy probes Doug about his ties to Christian, prompting him to reveal the intended hotel site on Roosevelt Island. However, as evening falls, Doug learns Christian is dining with another woman, prompting him to return and console Andy instead of revealing the betrayal. At a fancy dinner, as sparks between Doug and Andy begin to fly, their moment is interrupted by a call from Christian asking to meet her in their usual suite at the Bradbury.
Back at the hotel, Andy rebuffs any ideas of a romance with Doug, dismissing him for seemingly playing the part of Christian's "houseboy." Nevertheless, Christian provides Doug with the good news of his IRS troubles being resolved and commits to backing the hotel project. As tensions mount, Doug overhears Christian admitting to Andy that he has left his wife, casting doubt on their future.
During a high-profile fashion show later that week, Christian hands Doug the crucial paperwork that signifies the transfer of the lease to his corporation, thus ending the IRS audit. Doug brings up the notion of Christian's pending divorce, but Christian assures him that his wife has permitted him to pursue affairs as long as he maintains the marriage. Trusting Christian, Andy eagerly departs with him for Italy, leaving Doug torn.
In a twist of fate, Doug, fueled by determination, tears up the papers and masterminds a traffic jam on the Queensboro Bridge to confront Andy. Riding a borrowed horse from a hansom cab driver, he races against time to reach her. Meanwhile, Andy uncovers the truth behind Christian's scheme with Agent Drinkwater to mislead Doug and reclaim control over the property. Realizing her folly, she exits the car only to spot Doug running towards her across the bridge.
Moments later, Doug and Andy tie the knot, symbolizing the triumph of love over deception. Excitingly, Doug receives a phone call from Mr. Wegman, a guest whose marriage he helped rejuvenate, who expresses interest in funding Doug's hotel venture upon learning of his plans. The story culminates in a heartwarming final scene where Doug and Andy share a passionate kiss in the lift at the Bradbury, affirming their dreams are now intertwined with their love story.
