This year is the 10 year anniversary of the release of Flirting, looks like it came out in '96 (according to IMDB).
On a purely writer-director geeky note that may be completely wrong, I think there were several moments in Flirting where some of the material may have come directly from Russell's life - like when Stiller's character's wife, played by Patricia Arquette, loses her car keys in the dessert. If I ever talk with Russell I will have to ask him if that was just something that he came up with or if that was from real life. Some moments in the movie feel classically Hollywood & good: wild, spectacular, and some moments feel indie in a very good way: observed, reflected on, well thought out. Flirting is an incredibly well written, well thought out movie. A good combination of what's best about indie & Hollywood. I wonder if I can make something as good as Flirting. Should try.
If you haven't seen Flirting in a while, or at all, check it out.