It starts off well enough. This film, from the directors of There's Something About Mary, is all set to provide a humorous commentary on the dangers of listening to others when it comes to important, life-altering decisions. It chooses to illustrate its point through Eddie (Stiller), a 40-year-old bachelor who, although wary of the permanence of marriage, follows others' advice and ends up unhappily hitched. The film begins nicely by highlighting the necessity and fragility of compatibility in an intimate relationship.
However, the film falls short of its promised delivery. It instead degenerates into chaos and absurdity. First of all, Stiller and Monaghan (Eddie's extramarital love interest) lack the chemistry to convince the audience that their connection is strong enough to break up Eddie's marriage. Second, there are moments -- and then entire episodes - that do not cohere with the plot. Halfway through, the film just gives up all pretenses of plausibility and flow. The comedic moments fail to mesh with the dramatic plotlines, resulting in an unbalanced presentation.
The result is that the more The Heartbreak Kid tries to be outrageous and funny, the more it bores.