Louis Ives is a lonely dreamer who fancies himself the hero of an F. Scott Fitzgerald novel. When a deeply embarrassing incident forces him to leave his job at an exclusive Princeton prep school, Louis heads to New York City to make a fresh start. He quickly finds a nine-to-five job at an environmental magazine, where he encounters an entrancing, green-obsessed co-worker Mary. But it's Louis' new home life that really sparks his imagination. He rents a room in the ramshackle apartment of Henry Harrison, a penniless, wildly eccentric but brilliant playwright. When Henry's not dancing alone to obscure music or singing operettas, he's performing - with great panache - the duties of an "extra man", a social escort for the wealthy widows of Manhattan high society. These two men, separated in age by more than forty years, develop a volatile mentor/apprentice relationship. Through a series of urban adventures where they encounter everything from a leaping lion to a wildly jealous hirsute neighbor, from drunken nonagenarians to a shady Swiss hunchback, Louis & Henry form a memorable bond that may bridge their differences.
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Over the course of one raucous night at a seaside wedding seven close friends, all members of a tight, eclectic college clique, reconvene to watch two of their own tie the knot. Laura (Katie Holmes) is maid of honor to Lila, her golden girl best friend. The two have long rivaled over the groom, Tom. Friendships and alliances are tested and the love triangle comes to a head the night before the wedding, when the drunken friends frolic in the nearby surf and return to shore... without the groom.
