The Fun Parts by Sam Lipsyte
My rating: 4 of 5 stars
Sam Lipsyte has an ability to make me laugh uncomfortably, the way you would do after having a shared awkward experience where someone loses it in front of you. The characters in his short stories are always out of place, trying to cope with reality, failing, and the author is not afraid to push their scenarios to the most outrageous conclusion.
My favorites - The Climber Room (for the ending), The Wisdom of the Doulas (is the male doula "doulo" crazy, or is the world?).
Also - don't have kids. We forget, when we are grown up, how serious life was in our teens and pre-teens. Lipsyte hasn't forgotten, and it is terrifying.
To be honest, I really did enjoy these stories, but I liked The Ask even better. Short stories tend to vary in audience and tone, and not all of these had the same punch. The entire novel of The Ask did that for me. I'd start either place if you are new to his work.