The film begins at a fancy party at a rich person’s house, who is revealed as Edward Lewis, the corporate raider that buys companies in financial difficulty. He is heard on the phone to his girlfriend, who is complaining that she speaks to his secretary more than him. He asks her to be there for him with the following difficult week, and she refuses. They break up. Edward meets a pretty lady downstairs and it is revealed that they are old flames. It is evident Edward works a lot and has little time for his girlfriends.
Edward needs to leave and takes his partner Philip Stuckley’s new, and flashy new car. He drives down many roads and gets lost along the way trying to get to Beverly Hills. He ends up on the Hollywood Boulevard, where there are prostitutes and drug dealers.
The scene switches to Vivian Ward, an attractive young woman getting dressed for a night shift as a prostitute. She is seen coloring in her patent boots, and it is evident she has little money. In between, Edward is seen going down the wrong roads. Vivian climbs out the window as she has not money to pay her rent. She goes out to work on Hollywood Boulevard.
Vivian goes in to the Blue Banana Club to find her friend, Kit. She shouts at her because she spent the rent money on drugs. Vivian makes it clear that she hates this life. Meanwhile, Edward is lost and looking for directions to get to Hollywood Boulevard. The two prostitutes talk about how they take control of their profession by saying when, who, and how much. Kit encourages her to go for Edward in his posh car. He asks Vivian for directions, and she charges him $20. Vivian gets in and shows him the way. Vivian is enthusiastic about the car and Edward lets her drive it to the hotel. He drops her off and she sits waiting at a bus stop.
Edward originally goes in to the hotel, but then decides to hire Vivian and comes back out. He covers her with his coat and invites her in to the hotel. Vivian is evidently out of place in the very posh hotel. They arrive at his penthouse, and Edward reveals he is scared of heights, and never goes out on the balcony. Vivian tries to initiate sex, but Edward wants to talk for a while with champagne.
Edward begins to realize she isn’t like other girls when Vivian takes a break to floss her teeth. She watches old TV programs until Edward finishes work. They begin intercourse, and Vivian refuses to kiss him on the mouth. They spend the night together.
Edward's company is currently involved with taking over a company from the reluctant James Morse, and needs a companion to take to many social events over the next week. The next morning, his partner Phil urges Edward to go to the evening dinner to see James and his grandson with a date. Edward asks Vivian to spend the week with him as a professional without any romantic hassles.
Edward gives her some money to go shopping for some conservative and professional clothes. Once he leaves, Vivian rings Kit and tells her the news. She goes to Rodeo Drive to shop and is told to leave a shop because she looks like a prostitute with no money and they tell her ‘you’re obviously in the wrong place’. She returns to the hotel, and is asked by Barney Thompson, the manager, to not visit any more clients in his hotel. When Vivian tells him she couldn’t buy any clothes, he refers her to Bridget, who helps her to find a dress.
The film moves to Edward’s office, where it is revealed that James Morse has a new business deal, meaning buying the business will be a lot more expensive. Vivian buys a cocktail dress, and returns to her room. She agrees to meet Edward in the lobby in 7:45pm. Barney teaches Vivian dinner table etiquette, in preparation for her evening meal.
At 7:45pm, Edward meets Vivian in the lounge, and he is astounded by how beautiful and elegant she looks. They go to dinner with James Morse and his grandson David. She has a starter that isn’t a salad (the only fork she knows), and uses her hands when James does too. Upon eating snails, Vivian flicks the snails and generally struggles with dinner etiquette. James Morse asks Edward to leave his company alone, and that he will buy all of Edward’s stocks in his company. The deal that James was soon to have is now buried under paperwork in the appropriations department, where Edward has a contact.
Later, on the penthouse balcony, Vivian suspects that Edward likes Morse. They agree to not get emotional about business, either his or hers. Edward goes downstairs to think over the evening. At 3am, Vivian goes down to see where he is. He is playing the piano passionately. They get intimate on the piano, but Vivian refuses to kiss him. They go to bed.
The next day, Vivian tells Edward her troubles with shopping. Today, he goes with her. In a shop, Edward tells the manager he will be spending a lot of money in there, and Vivian gets fussed over by lots of women. Meanwhile, Philip rings Edward that James is still refusing to sell so he goes to work. Vivian buys lots of new and elegant outfits. In an iconic scene, Vivian visits the store that refused her, and tells them they made a huge mistake.
Edward finds out that James has mortgaged everything with Plymouth Bank, and Philip encourages him to ring the bank. Edward is obviously having second thoughts from his conscience; he regrets that they don’t build or make anything. He returns home, and finds Vivian in nothing but a tie she got for him. They have a bath together, and Edward tells her about his past and his issues with his Father.
The next day, Edward takes Vivian to the polo his company sponsors, where David Morse is playing. He introduces her to Phil and his wife, Elizabeth. They go and stamp the dibbets back in to the polo field. Vivian sees David, and she meets his horse. Phil interrogates Edward about Vivian and her job, as he suspects she’s a spy for the Morses. Edward has to tell him she’s a hooker to stop him from calling her a spy, and Phil laughs at him. He goes and taunts Vivian about it, asking for her services after Edward leaves.
When they return home, Vivian is mad that he told Phil about her profession. He shouts at her, and she leaves after he makes her feel cheaper than she ever has. He leaves money for her, but she doesn’t take it. As she’s waiting for the elevator, Edward comes out and apologies. After deliberation, she returns with him. After intercourse, Vivian tells Edward about how her awful dating history landed her in Hollywood. She couldn’t make the rent, and after meeting Kit became a prostitute. She reveals how she cried the first time she worked.
The next day, Edward leaves work early to go on a date with Vivian. She wears a stunning red dress, and he takes her to the opera in San Francisco via private jet, after giving her a loaned diamond necklace. Vivian loves the opera, and cries at the last song. Over chess, Vivian persuades Edward not to work the next day.
This is the day they start to fall for each other. They go to the park, and Edward reads Shakespeare and Vivian doesn’t let him work. They look like a proper couple. They go to bed, and Vivian kisses him on the mouth. As they fall asleep, Vivian tells Edward that she loves him. He hears but says nothing.
The next morning, they lament that this night is their last. Edward asks to see her again, and tells her he has organised an apartment and car for her in New York to get her off the streets. She feels as if she will just be a go-to girl when he’s not working. She tells him that she wants a knight on a white horse to save her, not a sugar daddy. Edward receives a call from Phil, and goes to meet James Morse. He tells Vivian that he cannot offer her the romance she wants right now, and she feels even more like a prostitute.
Kit arrives at the front door of the hotel, and asks for Vivian. Kit tells her she never fitted in on the Boulevard, and Vivian tells her she doesn’t want to see Edward again. Kit can see that Vivian is in love with him and tries to convince her it could work out.
In a meeting between Edward and Mr Morse, James tells them he has re-considered buying. Edward requests he speaks to James alone. Edward asks to buy his company, instead of buying it and taking it apart. James tells Edward he is proud of him in a Father figure moment. Phil is angry at the decision he was not consulted about.
Edward goes for a walk, and Phil goes round to the hotel to speak to him. He is greeted by Vivian, and he tries to sexually assault her as he blames her for Edward’s change of heart. Edward comes in just in time, punches Phil, and throws him out. As Edward ices Vivian’s face, she praises him on his decision with Morse. Vivian wants to leave, explaining that there will always be a guy like Phil who will think they can treat her like a whore. She explains she wants the fairy-tale, and Edward tells her it is impossible. He pays her, and she begins to leave. Edward stops her, and asks her to stay the night without pay, but she refuses. She leaves, saying goodbye to Barney. She returns to her apartment with regret.
Vivian packs her bag to go to San Francisco and finish high school. She hugs Kit goodbye and gives her money, telling her she has potential. Edward leaves the hotel, asking Barney to return the necklace. Barney tells him that Daryl drove Vivian home the previous day, insinuating he knows where she lives. Before Vivian leaves, she hears a car horn out the window. When she looks, Edward is standing out the top of his car, holding flowers, playing opera and proclaiming his love for Princess Vivian. Despite being scared of heights, he climbs the scaffolding to get to her. They kiss, and live happily ever after.
The film ends by a bum proclaiming that Hollywood is where you chase dreams, and to never stop dreaming.