From his Q & A with Alexandra Alter at the Wall Street Journal:
WSJ: Your parents were both writers – your mother was a journalist and novelist, and your father covered sports and has written young-adult novels. Did you always want to be a writer?--Marshal Zeringue
Mr. Lipsyte: I always wrote—probably initially in toddler imitation of my parents—through middle school, high school and college. Then I didn't write for a little while, and then came back to it… By the time I finished college,I was a little confused about what writing meant to me or what I thought of writing fiction. I got involved in a noise rock band and so I kind of screamed and drank for a few years. The rock band thing didn't really work out, as is so often the case.
How did you come up with the idea for "The Ask"? Where did Milo's character come from?
My novel before that was called "Homeland." When I finished that, I was living in Astoria, Queens, and playing around with a lot of different notions. I started to write about a character in economic distress, although there would be greater economic distress a few years later, and I'm not claiming I predicted anything.
I was interested in the theme of a character with his back against the wall.
You're known for writing dark comedies. How do you strike the balance between humor and some really depressing themes and circumstances?
I don't...[read on]
