Best friends Sam and Mike go out on a bender after Mike's long-time girlfriend Judy leaves him, for good this time. Meanwhile, Sam looks back on his own relationship, with the beautiful singer-songwriter Maria, and realizes how his actions may have been pushing her away. The Hedgehog Dilemma is a naturalistic, improvised film about communication, and the tragic inability of most humans to effectively connect with another person on a deeper, emotional level. Through Sam and Mike's relationships, we come to understand a bit about being young in the city, and the isolation faced by Generation Y.