Jake Singer (Chris Eigeman) personifies all the problems most men have when they're trying to commit to a woman. He just can't quite get the hang of it. He's a teacher at a Manhattan prep school and he should have everything going for him, but he often winds up on his hard-nosed, no-nonsense shrink's couch trying to figure out where it all went wrong. No amount of psychotherapy is cutting it, and everybody is just about to give up on the idea that Jake could straighten up and settle down. Then he meets Allegra Marshall (Famke Janssen), a well-to-do mother who -- one way or another -- just might make him see what "committed" really means.