Llama Llama Red Pajama is a good way to discuss both sleeping alone and separation from parents in general. It is definitely not the cure (in case you were hoping reading the book a few times would make bed time struggles a thing of the past) but it speaks to the possible worries of toddlers and preschoolers in a fun and creative way. I find that books that depict others (in this case an imaginative young llama) in their weakness allows my girl to voice her own emotions and fears. Books with slightly misbehaving characters allows my young one to gauge what is appropriate behavior and how her parent would react if she did the same – without going through the actual exercise herself. This book is helpful on both counts and my daughter loves it.