I was worried about this too when DD started going to a babysitter during the day when she was 10 months. But starting the first day, the babysitter got her to take 2 naps, no problem! She has been going to this lady for almost a year now and she says she just puts her down and she goes to sleep! We still can't do that at home, one of us (usually me) has to lay down with her until she falls asleep. I get jealous sometimes and want to know how she does it with 2 (another little girl goes there that is the same age as DD)!