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Sarah Michelle Gellar suggested that Alec Baldwin should play the role of Archie Knox.
According to director Marc Klein he knew that Sarah Michelle Gellar was the star of Buffy the Vampire Slayer (1997) but hadn't watched the series and didn't really understand its huge popular following. When shooting the outdoor scenes in New York, he was shocked when hundreds of fans, journalists and photographers turned up to watch her act in his film.
Vanessa Branch (Faye Faulkner) speaks fluent Mandarin Chinese and French, which was written into the script to make her character seem more intimidating to Sarah Michelle Gellar's character.
Based on the short stories "My Old Man" and "The Worst Thing a Suburban Girl Could Imagine" from Melissa Bank's book, "The Girls Guide to Hunting and Fishing". The book spent 16 weeks on The New York Times Best Seller List.
The opening scene was a reshoot done after production had wrapped. Sarah Michelle Gellar is wearing a wig because she had already dyed her hair back to blonde.
"Archie Knox: [sitting with Brett's family after meeting them for the first time] Well, I do appreciate the attempt you've all made at avoiding the obvious. It was a worthy effort. But let's cut to the chase, shall we. Robert, how old are you? Robert Eisenberg: 57. Archie Knox: And I'm 50. So, that makes me younger than Robert. So everybody feeling good about that right now? Ethan Eisenberg: I am very relieved. How old were you when Brett was in third grade? Brett Eisenberg: Grow up Ethan. Ethan Eisenberg: Brett skipped the third grade. Ethan Eisenberg: [imitates a buzzer] Well played."
"Robert Eisenberg: Is Archie alcoholic? Brett Eisenberg: Yeah Robert Eisenberg: Look, you know I don't like to get involved in your life. But this is the reason that I don't... That I'm worried about this relationship with this man. If Archie isn't going to take care of himself someone else will. I don't want you to have to spend your life that way."
