Ira Sleeps Over (by Bernard Waber)

Sleeping over for the first time represents a major milestone. Even if it's just a matter of going next door to spend the night with your best friend, it can, as Ira discovers, present some unexpected dilemmas. What if you take your teddy bear and your best friend decides you're a baby? Should you follow the advice of your parents or your older sibling, or your own feelings?

Ira's parents encourage him to do what he wants to do. But, perhaps more relevant for preschoolers, the story acknowledges that other people are not always so supportive. Older siblings, themselves (supposedly) newly liberated from a dependency on teddy bears, can zero right in on one's vulnerabilities with devastating effect. The artwork, pen-and-ink drawings with selective coloring, helps underscore the humor and has a little something extra for parents or older children returning to the book.