- Began acting in plays as a child at his synagogue.
- Wrote an original stage play, I Know You Are, But What Am I?, which he later adapted into his film All Over the Guy.
- Performed with the Groundlings improv troupe in New York.
- Wrote Lisa Kudrow's part in All Over the Guy specifically for her, after the two became friends while attending Vassar College.
- Wrote a book about being a gay parent called Does This Baby Make Me Look Straight? Confessions of a Gay Dad.
- Runs a production company, Is or Isn't Entertainment, with Lisa Kudrow.