1. Who is your favorite character in My Lucky Star? Do you find yourself drawn to the more conventional characters or the more outlandish ones? Are there any characters in whom you see qualities of your own, however exaggerated?
  2. What roles do Philip, Claire, and Gilbert play in their friendship? What does each one add to the trio? Does the way they interact remind you of any of your own friendships?
  3. My Lucky Star is great fun to read, but it's also a biting social satire. What vices/people/habits is the author commenting on? Which situations or characters did you find the most successful in this respect?
  4. When Philip volunteers to write Lily's memoirs, he infiltrates her scheme through the use of his own. When else does this sort of backstabbing happen in the book? What do these situations say about each of the characters involved? Is one motive better or more moral than the other?
  5. As the novel's heroes make their way through the maze that is Hollywood, Gilbert manages to get them into one sticky situation after another. Why are Claire and Philip always unable to put their foot down, no matter how hard they may try? Do you have a friend like this, who always creates trouble and yet whom you can't resist having around?
  6. From a faded film star to a backstabbing ex-wife, My Lucky Star's Hollywood is filled with characters out for blood. But how else is one to act in such a dog-eat-dog city? Are there any characters you sympathize with, despite their seemingly evil intentions? Discuss the motives behind each of the key players.
  7. Have you been to Hollywood? Do you think Keenan's depiction of the city is accurate?
  8. Do you like Keenan's swift and witty voice? What do you think comic novels offer us as readers, besides enjoyment? Do you find comedy to be even more telling than drama, or less?