La temporada 1 de Help Me Help You se estrenó el 26 de septiembre de 2006.

Dr. Bill Hoffman is a brilliant therapist with a lucrative practice and the author of several definitive psychotherapy texts. But his over-inflated ego is dealt a blow when he is forced to come to grips with the end of his 25-year marriage to wife Anne. Bill is also forced to deal with the news that his daughter is dating her psychology professor. Things are changing too fast, and Bill is struggling to keep up.

When it comes to the group patients, Bill also has his work cut out for him: The newest group member, Dave, recently attempted suicide by jumping out of his office window—and landing on his boss; Jonathan is a self-avowed metro-sexual who is in serious denial that he might possibly be gay; Inger is a 25-year-old, self-made millionaire who totally lacks social skills and hasn't had a real date in over six years; Darlene has too many psychological issues to count, including her obsession with Dr. Hoffman; and Michael has anger issues at work, which is what led him into mandatory group therapy.