Wanted: true love and self esteem

"Prep," Curtis Sittenfeld's meticulously imagined first novel, told us everything we ever wanted to know - and many things we didn't - about a painfully insecure, self-sabotaging adolescent's passage through a fancy prep school.

Toward the end of her 400-plus-page odyssey through four years, "Prep's" narrator, Lee Fiora, claims that when she left boarding school, she did not carry her "vigilance" with her: "I've never paid as close attention to my life or anyone else's as I did then." Hallelujah, some of us thought.

Sittenfeld, however, is still paying close attention. Her second novel, The Man of My Dreams, features another colossally insecure, self-sabotaging young woman. The good news is that Sittenfeld continues to address the angst of self- proclaimed social misfits with unflagging sensitivity and intelligence.

Better yet, Hannah Gavener's story covers 14 years in 266 pages, a less obsessive level of detail. All but the coda, an implausibly long letter to Hannah's therapist, is written in the third person. With "The Man of My Dreams," Sittenfeld inches into Melissa Bank territory, another writer who features self-deprecating single, young, women trying to find their way in love and life.

Sittenfeld, however, is less prone to use humor or charm to win easy sympathy for her heroine. There is nothing glib or sassy about Sittenfeld's prose.

And she certainly isn't afraid to show her characters in unflattering light. Hannah is so blunt that she makes a sledgehammer seem sharp.

Her reaction to her sister's engagement announcement is one of several appallingly tactless remarks: "I guess I just don't see him as very special," she says.

"The Man of My Dreams" starts in 1991, when Hannah is 14 and her parents have just separated, and ends in 2005, when she is 28.

Although it is definitely a novel, each chapter, as in "Prep" (and as in Bank's "The Wonder Years"), is lovingly crafted with a discrete beginning, middle, and end, a structure that more typically characterizes stand-alone short stories.

Sittenfeld checks in on Hannah at crucial points in her life: her freshman year at Tufts University, her first boyfriend, her mother's second wedding, a job that finally fulfills her. The supporting cast is sharply delineated.

Part of Hannah's problem is her father, the moody, bullying "weather system" by which she, her older sister, and her sweetly compliant mother live in Philadelphia until her mother bails out.

Hannah refuses to forgive him, but hates the fact that she's inherited his stubbornness. Growing up involves recognizing that not all her failures can be blamed on her unstable childhood. As in "Prep," Sittenfeld writes several powerfully fraught father-daughter scenes.

Hannah's distrust is so pervasive that when confronted with a consistently agreeable stepfather, she "is not sure what his personality is like." Her reaction to supportive, thoughtful Mike, her first lover, is antsiness.

Just having a boyfriend strikes her as oxymoronic: "Hannah's boyfriend - they will always be the weirdest words Hannah can imagine. Jumbo shrimp, she thinks. Military intelligence."

Hannah's inferiority complex is exacerbated by her pretty, kind sister and her seductive but often thoughtless cousin, who both manage to attract men and overcome adversity with such apparent ease. As in "Prep," Sittenfeld's heroine backs herself into a bad relationship because she can't believe she's worthy of her crush's affections.

Her cousin tries to be helpful. "Why not assume from now on, until you have evidence to the contrary, that every man you meet finds you irresistible?" she admonishes.

Hannah's sister notes, "You give too much attention to things that make you unhappy."

Hannah's response is what separates Sittenfeld from mere chick-lit writers. She writes, "No doubt she is on to something. And yet attending to things that make Hannah unhappy - it's such a natural reflex. It feels so intrinsic, it feels in some ways like who she is. The unflattering things she notices about other people, the comments she makes that get her in trouble, aren't these truer than small talk and thank-you notes?"

Readers are liable to cheer when Hannah's cousin prods, "Don't take this the wrong way, but it's time for you to lose your low-self-esteem shtick. It's gotten kind of stale, you know what I mean?"

There's nothing stale about Sittenfeld's assured, nuanced writing - so far - but we look forward to her moving past the "low-self-esteem shtick."

• Heller McAlpin is a freelance writer in New York City.