Plot: Approaching forty, Conrad Valmont has not worked a day in his life, he having lived off the wealth of his parents, who he has not seen of late as they are on a perpetual around the world trip. Conrad, however, tells people that he is working on the quintessential New York novel, it always being in the information gathering stages. Conrad grew up and still lives in the family's lavish, old world Manhattan hotel, where he was raised by servants. He has never been in a serious relationship, those available women he finding sexually attractive a bore, and those he finding interesting to who he is not sexually attracted. Whenever he has stayed with a woman for longer than one night has always been solely in not wanting to be alone. His longtime best and only real friend is equally wealthy Dylan Tate, whose money is self made as a successful artist, and who is a socialist at that. Also unlike Conrad, Dylan takes love seriously, he and his last girlfriend, Jocelyn, with who he just broke up, lasting for three years. Out of circumstance and without previous notification, Conrad's parents cut him off meaning that he has to move out of the hotel immediately with no money and find his own means of living. The subsequent week in Conrad's life is presented, that week which includes he: borrowing a couple of hundred dollars from his longtime therapist, Barry, to get him going; moving in with Dylan, who he does not tell about his new financial situation; falling in love for the first time, with Beatrice Fairbanks, a model and aspiring musician, she who happens to be the woman Dylan is also pursuing; and starting a clandestine relationship with Beatrice - a woman he could see being the one - despite vowing to Dylan that he would not hit on her, Dylan who could see his attraction to her. The primary questions become what will happen to Conrad's relationships with both Dylan and Beatrice when they inevitably find out about his financial situation and with Dylan specifically about breaking his vow concerning Beatrice, and whether during this week Conrad will take steps to truly growing up, something that has not happened in forty years.
Alternative Plot: Left broke and homeless by his wealthy parents' divorce, a young man (Jason Bateman) moves in with an old friend (Billy Crudup) and finally meets the woman (Olivia Wilde) of his dreams -- only to discover she's already dating his friend.
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