The film opens up with Chelsea, real name Christine (Sasha Grey), on a date with a man. They come out of a movie and have dinner together. The man discusses the movie they saw and tells Chelsea about problems in his life, including a friend who keeps borrowing money. They start to make out on the man’s sofa.
The next morning. A personal trainer, Chris (Chris Santos), is exercising with his client, Peter Zizzo. Zizzo asks Chris what he’s doing this weekend and Zizzo implies that he wants to hang out with Chris. Chelsea is asleep in her bed next to the man she was on a date with. She gets up and walks to the bathroom. Her date wakes up and orders them some breakfast while she applies make up. They talk about the economic bailout before the date reveals that he pays Chelsea to date him. They agree to stick to cash payments. This is then followed by a group of businessmen (with Chris and his client, Zizzo among them) on a plane discussing Obama and the crisis facing the economy.
Chris is running through New York City after work and arrives at his apartment as Chelsea leaves her client, Phillip, to his work. She gets into a car and begins to account what happened the night before. She describes what she was wearing and how the sex was to the driver, and indicates that in her line of work she provides the full experience of having a girlfriend. They went to Man on Wire and then talked before sex. She notes Phillip’s very awkward goodbye and that he didn’t make another appointment. Chelsea notes that if they wanted her to be “real” they wouldn’t be paying her.
Chris talks to Zizzo about the payment package Zizzo pays for each week and tries to convince him to buy in bulk to save money. Zizzo then tells Chris that he should come to Vegas with him and that he (Zizzo) is willing to pay for Chris. Chris agrees and gets dressed in a suit and tie before receiving a package. Chelsea is in the apartment and the two are ready to eat dinner. Chris tells her about Zizzo’s suggestion for a “Boys Trip to Vegas”
Cut to Chelsea talking to various clients about the economy, business and her job. She goes over the basics and serves as a confidant for men who don’t have anyone to talk to. After talking for a bit, she usually sleeps with the clients. Chris goes to a meeting with several businessmen to try and sell his product to a large market but the businessmen are hesitant.
Chelsea meets with a webmaster in order to get her website more traffic so that she can make more money from her escort service. The man tells her that he can work monthly and she agrees. "The Erotic Connoisseur" calls her and offers to help her reach more high class clients. She is hesitant to agree to this despite the Connoisseur’s offer. She meets with the Connoisseur for lunch and he tells her that with the state of the economy, she should meet with a man who knows the most about her business market.
She meets with the Connoisseur’s contact and they talk about expanding her business into boutiques and other lucrative branches such as books and movies. Chelsea expresses her doubts at this and then meets another escort named Tara as she leaves. She meets with another client who just talks about their past sessions but doesn’t sleep with her. During another date, one of her clients sees her on the job with another client and they have an awkward exchange. On the plane, Chris goes through a similar experience as the “paid escort” of the guys on their way to Vegas. Zizzo points out those men who pay to have women around know that deep down the girl isn’t interested in anything but the money.
Chris meets with the head of Club Fitness and asks about whether or not they are looking to expand. It’s clear that Chris needs to make more money and he’s looking around for more money. He goes to his boss and asks if there’s a way to increase his money and start taking a larger role in his own gym. His boss tells him it’s the worst time to ask for a managerial role, but Chris makes it clear that it’s the right time to ask just in case things get worse. His boss expresses doubts at Chris’s managerial potential because of the fact that he is “too independent” within the gym.
Chelsea goes and buys a prepaid phone and calls a client from L.A. who is visiting New York. She talks to him, asking about his family life and job in order to get a feel for him. He asks to meet tonight but she makes it clear that she’s busy and asks if it’s his first time. She tells him that she has a rule that she never caters to people who have never hired an escort before but decides to make an exception for him.
She meets with a friend and discusses the fact that she clicked with the client. She makes it clear that she is going to leave Chris and that she has enough money to be financially independent. Chris and Chelsea have an argument after Chelsea tells him she is leaving him for a married businessman. Chris tells her that the man will use her for a weekend and then leave her and go home to his wife and family.
He tells her that when she’s left high and dry, she won’t be able to come back to him because she ended it. Chris then goes to drink with his friend and mourns the end of his relationship with Chelsea.
Chelsea meets with the Connoisseur again and he makes it clear that he wants to try her out before he takes Chelsea on as a part of his business. Chelsea is creeped out by this and tells that to her friend. Chelsea goes and shops for new clothes and apparel. As she’s shopping she sees a girl with Phillip and realizes that Phillip has hired a new, younger escort to take over her job. She meets with the client she dumped Chris for and realizes that, while there are boundaries, she genuinely enjoys spending time with him. The client tells her that he doesn’t want to go home and asks if she wants to go away for the weekend. He tells her that he’ll send a car for her and that they’ll see how the weekend goes.
Chelsea goes to a gym and starts working out. She withdraws some cash and gets a makeover. The client calls her when she goes out to the place they were supposed to meet and tells her he has to go home to his family. He apologizes and tells her that when he remembered his kids, he ended up crying and realized he had to go home. The Connoisseur gives her a very harsh review and calls Chelsea the “Nader of Passion” which is designed to hurt her business and give more business to the new girl on the street.
Chris goes to Vegas with the businessmen in order to forget about Chelsea. The group arrives in Vegas and check into their luxury hotel. They party and meet a lot of women and Chris mingles with a bunch of them. Meanwhile in New York, Chelsea is walking down the street alone and meets with a ghost writer who wants to learn about her and her business, especially the fact that she was in a committed relationship while she worked as an escort. He asks her what kind of person gets under her skin considering her line of work. She says that while most people don’t get under the outer layer, once in a while someone does.
She leaves the meeting and goes on to her next client, making it clear that it is business as usual.
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