wildflowersoul

We tried that once (going out after he went to bed) and it didn't work super well, but that was back when he was a very bad sleeper (as opposed to just being a not-great sleeper now). We usually go out around 6-ish, so he will have eaten dinner and I get him jammied before leaving, the sitter just has to entertain him quietly for an hour, read him his bedtime stories, and put him to bed. This time we left at 4, so the sitter had to give him dinner, entertain him more, and do the whole jammies/diaper/stories bedtime routine. It seemed to work out fine, amazingly enough. He actually goes to sleep really well for sitters now, even if they are total strangers. We've had good luck with Sittercity.com and now we have a couple of Endicott College students we can use. Though even the college students are charging $12/hour, so it's not something we can do that often.