Winifred Wilkes first appears in Season 3. (One More Last Chance) She is a strong and opinionated women who states she hates New Yorkers because her exes seem to be tied with the negativeness of the city. She loves family. She takes a strong liking to Wade Kinsella; and a strong disliking to Zoe Hart and Joel Stevens.
- Winifred is one of the shows first open gay characters.
- "Oh, tell me about it. It's always a spitting contest. Young boys, old boys, you name it. That's why I just tabled the entire gender." --A Good Run of Bad Luck