Jonathan Levine’s comedy is set in Manhattan in 1994, and that particular setting is at least three-fourth’s of the movie’s premise. The story set against this detailed backdrop involves Luke Shapiro (Josh Peck), who is one summer away from heading off to college. Meanwhile, he deals drugs and romances his psychiatrist’s popular stepdaughter, Stephanie (Olivia Thirlby). There’s a class issue and she’s way out of his league, but eventually she gives him a tumble anyway. He loses his virginity to her and so believes he is madly in love, and awkwardly phone-stalks her. Meanwhile, his shrink, Dr. Squires (Ben Kingsley, in a twitchy, heavy-handed, nearly unwatchable comic turn), is being divorced by Stephanie’s mother and so he makes Luke his mid-life crisis best buddy.
All of this adds up to a fairly uninteresting and unoriginal movie, with a few touching scenes (including a beautifully acted, if pointless, part by Jane Adams, who needs to be given a good project, already). Nothing it has to offer, however, is even remotely worth viewing Mary Kate Olsen making out with Ben Kingsley – I really could have lived my whole life without seeing that.