There are so many wonderful ways for a girl to go wrong in the modern era. Katie Kampenfelt (Britt Robertson) is a prime example of this. With confusion and uncertainty pervading her spirit, Katie opts to defer college for a year in order to "explore other options," which, of course, really just means exploring her sexuality.
In between having sex with her "steady" boyfriend and having a dalliance with a college professor named Dan Gallo (Justin Long), Katie has a very busy schedule. As Allison Burnett's (a man, in case you were wondering) first directorial effort, adapted from his own novel, Undiscovered Gyrl (incidentally, the name of Katie's blog), Ask Me Anything puts a lot of pressure on itself to be taken seriously. As a result, it often comes across as just the opposite, though there are memorable moments of poignancy.
Katie's desperate desire for male attention, naturally, stems from her father issues. As a former sports writer and constant alcoholic, Doug (Robert Patrick) has very little interest in life other than the bottle. Thus, to Katie, who visits him on a regular basis in spite of living with her mother, it feels as though she's constantly being ignored and neglected. As a part of her quest for both mental well-being and a bit more attention, Katie starts a blog detailing all of her sexual escapades. The result? An adoring and hateful fan base.
One of the few men in Katie's life who doesn't judge her is her boss, a bookstore owner named Glenn (Martin Sheen). Unfortunately, after Katie's mother's boyfriend does a background check on Glenn, he discovers that he's a sex offender and demands that Katie quit. There's only a brief period of unemployment, however, until Katie is asked by Paul Spooner (Christian Slater), a man she met during one of her college interviews, to take on a job as a nanny to his newborn son. It is at this point that Katie goes off the rails in terms of sound judgment by engaging in an affair with him even though she's actually rather friendly with his wife.
It's almost as though Katie's sexual prowess is her true art form--the one thing she's really good at. In fact, she even confesses to Glen regarding herself and her generation, “It’s like we all wanna be famous even though we’re not good at anything.” This self-deprecating, yet unapologetic admission is the crux of why Katie is so miserable and dissatisfied. The twist at the end is, indeed, her best and only attempt at living on her own terms in a way that will allow her to be happy. Not so surprisingly, this involves getting off the internet.