That The Heartbreak Kid manages to synthesize May's improvisational satire, Simon's situation comedy, and [the bitterly black humor of Bruce Jay Friedman's "A Change of Plan," from which The Heartbreak Kid was adapted], and emerge as an occasionally brilliant, if indecisive, American comedy is an achievement very much out of the ordinary. Furthermore, Elaine May's second directorial effort is carried off with such a casual comfort and buoyant pace that the contrasting threads are only rarely visible…. [The] one consistent quality found in The Heartbreak Kid is the ability to take us by surprise—which is above all what makes this movie one of the few really enjoyable comedies by a young American director in recent years. (p. 60)

At the core of The Heartbreak Kid is a serious moral dilemma. This dilemma hinges on whether Lenny is correct in cruelly dumping Lila in order to pursue his dream girl. Neil Simon's traditional response to complex human relationships is to pass them off with a gag line, and it is to Elaine May's eternal credit that she did not allow The Heartbreak Kid to deteriorate into Barefoot in the Park. By lingering on the characters for a brief moment after the scene's punctuation with a joke, she enables us to see that the humor coincides with confusion and sadness. Framing the film with almost identical weddings, down to the music …, also reinforces the lack of resolution in the intervening comedy. The most disturbing aspect of Simon's comedic formula in the past has been his tendency to give his hand away, to anticipate his own punch line and rob us of the joy of discovery. May's gift has been quite the opposite; she lets us believe that she is guileless, totally distanced from the humor in the situation. In the role of innocent participant rather than sophisticated commentator, she allows humor to evolve where Simon's dissolves. The Heartbreak Kid permits Simon his pokes in the ribs, but May's emphasis falls on the side of the people involved. Like Lenny himself, The Heartbreak Kid manages to win one over by virtue of its surface charm. Unlike the film's rather dubious hero, however, the film has a lot going on beneath the exterior. (p. 61)