Lyle Finster, played by John Cleese. The father of Stan's mistress, Lorraine, oddly became Karen's fourth husband for about 20 minutes until the couple realized how little they had in common outside of the bedroom.

Scott Woolley, played by Jeff Goldblum. The man who lost to Karen for School Body President, and has spent his life hatching schemes to ruin her. Sadly, his schemes are often poorly thought out and eventually Grace realises that he doesn't hate Karen, he loves her. However his attempts to woo her are as misguided as his previous ones. Woolley also has a dreadful sense of word-play (i.e. "The Scotty Mammoth", "Beam me up, Woolley"). He also changes his first name when using an alias, whereas most people change their last names.

Lionel Banks, played by Rip Torn. A bachelor who falls for Karen, under her alias Anastasia Beaverhausen, while Stan is in jail, and tempts her into having an affair.

Malcolm Widmark, played by Alec Baldwin. A government agent who helped Stan fake his death, he had a brief relationship with Karen before she reconciled with Stan, and Malcolm went on a government mission to Sri Lanka.