However ironically, Lucinda Rosenfeld bills her first novel as a list. Its clever title is followed by a table of contents– fifteen chapters for fifteen-plus guys, including Anonymous 1-4 and Nobody 5-8. This turns out to be the index of Phoebe Fine’s pathetic love life from pre-pubescence to young adulthood, a series of unflattering portraits of unflattering boyfriends, and a collection of explanations as to what she saw in the mirror.

Phoebe’s romantic miseries begin as early as fifth grade when her first crush–bad boy orphan Roger "Stinky" Mancuso, whose favorite expressions are "Ya mental?" "Ya gay?"–moves away. Despite high achievements in tennis and violin–important assets in the upper-middle-class New Jersey suburbs of her youth–Phoebe, largely ignored by her classical musician parents and goody-good older sister, feels invisible to all but pimply nerds. So when high school heartthrob Jason Barry Gold begins to pursue her, even her so-called best friend is shocked.

Winning Jason’s friendship and respect (by refusing to have sex with him) does nothing to boost her self-esteem. Where once she tried hard to preserve her virginity, after Jason she creeps off to college desperate to lose it. Veering wildly from extreme to extreme is Phoebe’s pattern. When frat boy "Spitty" Clark is too busy retching to deflower her, she runs away from her sorority in the middle of the night to look for sex among the Eurotrash. When self-proclaimed anarchist and feminist studies major Humphrey Fung is no longer amused by a starving, doting girlfriend, Phoebe chases her fantasies off to France and bulimia. A long, degrading affair with an older, married visiting professor who watches the television before intercourse is followed by a fling with a grunge musician who has nothing but television to talk about. Then, unlike most girls with Phoebe’s track record, she’s naïve enough to get duped out of her life savings by a man promising to make her a star. No better judgment ensues. The next mistake–unreliable artist Pablo Miles (formerly Peter Mandelbaum)–leads to the next and the next.

The challenge of writing about such a passive character without making the writing itself passive is mostly met by the book’s brisk pacing and Phoebe’s self-awareness about her own insecurities. At eleven, she’s already conscious of how telling a friend about a kiss far exceeds the experience. At nineteen she makes herself "hot by association" by landing the boy all the other girls want. "And with every new guy there was new proof–that she was ‘incredibly gorgeous.’ Because she was never so gorgeous–not even when she was ‘incredibly gorgeous’–that she didn’t require outside confirmation."

Of course, knowing yourself isn’t the same as helping yourself. Phoebe can’t or won’t change. Fortunately or unfortunately, a string of one-night stands is punctuated by a skin disorder (which means forced abstinence). A string of horrible (hilarious one-liner) dates is punctuated by a "real" boyfriend, Neil Schmertz. A string of comfortable months is punctuated by such excruciating boredom that Phoebe amuses herself by fantasizing about Neil’s death. But just when the reader is out of hope, the next beau, Bo Pierce, appears on the subway. Better yet he appears, disappears, and reappears a la Prince Charming. At last, Phoebe is (maybe) saved!?

If this sounds like "lite" reading, it’s not. Rosenfeld, an accomplished journalist, presents a view of modern romance that is heavy hearted and full of grit. But her graceful and deceptively simple prose style flows quickly, delineating between and vividly capturing each of the duds in the line up: "He had the kind of hair that attracted fluff and string." "He smelled clean. He looked competent, too. As if he’d know what to do in a crisis in a fire, or a robbery, or an elevator that got stuck." "Four months later she could barely remember his face, but his hands, his simultaneously chapped and greased hands, she couldn’t forget."

But the book’s virtues are often tied up with its drawbacks. A real page-turner, it’s too relentlessly depressing to really qualify as beach reading. One can only assume the narrator is being sarcastic when two-thirds through this catalog of despair (sorority girls painting "FAT" on her thighs, a boyfriend who doesn’t care if she sleeps with his roommate) she writes, "An ugly period of Phoebe Fine’s life was to follow." The humor, while original and, at times, deeply funny, is always the kind that makes you wince.

A book full of sex, it offers up the action without much contrast. Here intimacy usually results in pain or humiliation, boredom or disgust. Vomit. Rug burns. Weight gain. And, while a perceptive story about Phoebe’s chronic inability to connect with others, it lacks the character development that would give it a satisfying shape. Phoebe can’t evolve because she despises herself too much to learn from her mistakes. What she saw in all of these losers is beautifully explained but basically redundant–someone to validate her body and therefore validate her otherwise empty existence. What we see makes us feel like rubberneckers.

No doubt, all this was Rosenfeld’s intention. In its candor and focus, the book reaches for something true and novel. And it is, at least, true and original. The question might be: Is it a novel? Is there enough craft added to these truths? Is there enough distance between author and subject to turn life’s acutely observed minutia into a sustained fictional narrative? By choosing a list as a structure, did Rosenfeld write herself into a dark corner?

To me, the book is most successful in isolated chapters, as linked short stories. Several chapters, particularly "Anonymous 1-4" or "Overheard in Bed During Phoebe Fine’s Admittedly Short-Lived Experiment with Promiscuity" and the letters (from her mother and to a foreign pen pal) are stunning prose poems in themselves. The hard-edged tone that meshes so perfectly with the later adult sections (recently excerpted in the New Yorker) seem too harsh when applied to the shy adolescent. The suddenly upbeat ending, while a reprieve, felt a bit tacked on, its message hazy. Love is a bore, infatuation rules? Love is a lottery with better odds for the better looking? If you spend all your energy on trying to be sexy, someday your prince will come? Phoebe’s quest to find a man (and thus herself) will resonate with most young women and enrage any feminists who insist on reading it literally or politically. And that’s no small feat. If Lucinda Rosenfeld can write a list this harrowing, imagine the novel she has in her.