Some Prefer Cake (1998)

In San Francisco, Kira has a day job at a warehouse, writes jokes for her sister (who does stand-up back East), wants to perform her own material, hangs out with best friend Sydney (who writes food reviews), and sleeps once with every woman she can. Then, her roommate sets her up with Robin - who's recently come out and hasn't had a serious relationship yet - and her friendship with Sydney gets rocky. Meanwhile, Kira's being stalked by one of her one-night stands, her sister isn't showing any appreciation, and a night at an open microphone goes badly. Is this all life can offer?