The film is based on the short stories by Max Shulman collected as The Many Loves of Dobie Gillis (also the title of the later TV series).

[2] At the time of release, a Philadelphia Inquirer reviewer called the film "agreeable" and cited Van's "rubber-legged grace, reminiscent of Ray Bolger.

[6] The Los Angeles Times called it a "lightweight, lightheaded comedy," and said the Max Shulman screenplay "is, shall we say, charitably, innocuous,"[7] The Pittsburgh Post-Gazette called the film "a small musical" that was "hung on the weakest imaginable plot," and said that it was "an insignificant piece of fluff" that was "hardly up to the standards of its principals, all of whom seem entirely too attractive and talented to be bothering with such nonsense."

[8] More recently, an Allmovie review criticized the film's "desperate, artificial perkiness -- the kind of Hollywood-derived energy that annoys by its phoniness."

The review goes on to say "Ultimately, though, the trite (and often unbelievable) situations, lame jokes, and banal dialogue overwhelm the good will that the musical numbers engender.

Extremely undemanding audiences, or those with a very strong nostalgic bent for the good old days, may enjoy The Affairs of Dobie Gillis, but most are advised to give it a pass.