Lee Fiora, the heroine of Curtis Sittenfeld's extremely heralded debut novel, Prep, is not exactly what one would call confident. She has trouble making friends at her uber-prep school, the fictional Ault, and wonders out loud several times throughout the tome why anyone (male anyones especially) would ever like her. Even with her borderline over-the-top self-loathing, Lee remains oddly endearing. You're rooting for the dorky girl from Indiana to get the guy, to pass the class, to emerge triumphant from the stodgy, WASPy halls of Ault with at least a modicum of chutzpah.

In her new novel The Man of my Dreams, Sittenfeld presents the reader with a similarly self-loathing heroine in Hannah Gavener. But this time around, the low-self-esteem ridden antics of Hannah fail to incite the same kind of identification and pity that Lee so easily wrangled from the reader in Prep.

Part of the problem is that for most of the book, Hannah is much older than Lee. The Man of My Dreams follows Hannah from her late pre-adolescence to her late 20s.  At the beginning of Prep, Lee declares fervently, "I would never have friends; the best I'd be able to hope for from my classmates would be pity." The kind of insecurity that plagues both these heroines is acceptable, almost charming in a high-schooler like Lee, but when the self-defeating behavior continues far past those hormone-addled teen years, it's painful.

When Hannah's in college, she has the same kinds of trouble Lee has making friends in high school, but her egocentric obsessiveness is harder to swallow. She has a crush on a possibly punky kid in one of her classes, and because he has a bad cough during discussion one day, Hannah decides to bring him a bottle of cough syrup as a friendly gesture. Cute, right? Not if you're Hannah Gavener. She spends the better part of two pages freaking out.

"As the minutes of class ticked away, Hannah felt a building, billowing regret, practically a nausea," Sittenfeld writes. "Why is she so fucking weird? Why did she give this punky boy she's never talked to expired cough syrup? Did she think she was flirting?" And so on.  After about 100 pages, Hannah's neuroses shift from endearing to annoying. “Why can't she grow up a little? Why does she insist on making her life so much more difficult than it has to be? Why does she let her British boyfriend walk all over her?” And so on. 

The British boyfriend, Oliver, is a particular low point for our girl Hannah. She had never felt good about herself, but her depression and judgmental nature always had a certain dignity about it. Hannah has a list of rules for Oliver. These rules include, not hiring prostitutes, not having sex with the same (other!) woman more than twice, he is allowed to receive oral sex but not perform it, he has to use condoms, and he has to shower before he comes to Hannah after his other conquests. It seems like the only thing Oliver is not allowed to do is have a threesome with two girls he's slept with twice before already. At least Lee, though she does subjugate herself to her crush, Cross Sugarman, has the good sense to stop fooling around with him once she knows for sure he's fooling around with other girls at Ault.

At the ends of their respective stories, both Lee and Hannah look back on their earlier low self-esteem and general chumpiness from the vantage points of being older, wiser and more self-assured, but with Hannah, her postscript comes in the form of a letter that constitutes the final chapter. It's a letter to her old therapist, and it's fairly unsatisfying.

While Lee's post-Ault reminiscing rings true, (everyone feels out of place in high school) Hannah's quick transition from doormat-with-crappy-boyfriend to beatific teacher of autistic children is less than believable. She makes declarations about her students like "Mickey is the most cheerful person I've ever known. I take him to the bathroom once an hour. He recently graduated from wearing diapers to Pull-Ups…When he sits on the toilet…he looks around the bathroom in such an upbeat, appreciative way that he calls to mind a businessman who has finally taken a long awaited trip to the Bahamas." After 200+ pages of self-loathing, I just don't buy that Hannah has really found peace through ministering to the potty needs of disabled youngsters.

In her new short story, "Volunteers Are Shining Stars," which appears in the excellent anthology This Is Not Chick Lit, Sittenfeld's unconfident, self-absorbed heroine Frances (a literary cousin of Hannah and Lee), crosses another line, this time from merely annoying into possibly violent. While Lee and Hannah are at least somewhat sympathetic, Frances is, well, a fruitcake.