Crosses the Line Twice: Dede steals Tom's ashes. How does she demonstrate this? By taking the urn out, turning it upside down and showing that it's empty. Lisa Kudrow's hysterical delivery of "where are the ashes?" is the topper.
Hollywood Homely: Lisa Kudrow is given drab brown hair and frumpy clothes to make it look like she's a plain woman. It's established that she used to be fat as well.
Dede is a real piece of work and she's an outright Villain Protagonist. But you see her crappy life at the start, and her narration seems rather bitterly accepting of how nasty she is. The viewer is led to believe she dies twice in the film, and both times are played sadly.
Lucia is rude and bitchy to everyone. But she has a Friendless Background and her only companion was her brother, and now he's dead. So she hangs around with his widow because he's her only friend. Dede even lampshades this as she flashes back to Lucia's unhappy teen years, saying that we may feel sorry for her as she eats alone at her sister's wedding - "but would you sit with her?"
Love to Hate: Lucia is so shrill and over-the-top that she's the favourite character in the movie.
"Seinfeld" Is Unfunny: Dede being a Genre Savvy snarky narrator was one of the main innovations of the film at the time. Roger Ebert heaped praise on the movie for featuring a protagonist that was aware of movie cliches and subverting them. Of course that sort of thing hardly seems new these days, and Genre Savvy characters popped up everywhere in the 2000s.
Stoic Woobie: Bill has to deal with his boyfriend dying, his sister having an affair with his current boyfriend, a smear campaign against his character and homophobia from his own students. Not that you hear him complaining about it.
Unintentionally Unsympathetic: The movie seems to paint Matt as a lovable character who just gets easily manipulated by Dede. But he still freely has an affair with his boyfriend's sister. Dede's conning of him comes across as Laser-Guided Karma.
Values Dissonance: It's hard to imagine a character like Jason appearing in a film these days. He's a Flamboyant Gay stereotype who causes all sorts of trouble for Bill. Dede's casual homophobia meanwhile is used to show her as a bitch.