Corporate attorney Leslie Cauldwell is middle-aged, handsome, and rich, but has only a few swipes left on his mental Metrocard. During a rough sex session, he garrotes his beloved wife; now he's an officially designated "sex offender," off on a bender, looking for love in all the wrong places. Twenty years earlier, when his office was high above the pornographic purgatory of Times Square, Leslie became involved with the adult-film star, Sky Pacifica. She needed a refuge, and he was ripe for the using. Following a brief fling, each went their own way. Two decades later, in 2001, Leslie is still working in Times Square--recently sanitized with its ESPN Zone and MTV window--and fraught with guilt about the "accident" with his wife.

Like Jay Gatsby pursuing an erotic American dream, Leslie, with the help of a private detective, hunts down Sky Pacifica, his latter-day Daisy. Across a landscape of S&M mistresses and porn producers, from L.A. of the '80s to New York of the new millennium, we see a modern-day tale of love and loss, innocence and corruption, crime and redemption.