At what age would you allow your toddler to have a sleepover with a friend? I'm not talking about when the whole family goes away, but when the toddler gets to sleep in a house where his parents aren't. We probably started younger than most would, but then his best friend lives next door, so his parents and us rigged up nannycams in the toddlers' rooms on a secured shared wi-fi so we could both keep an eye on them, whichever house they were in. That way we could let them have playtime upstairs while we had an adult chat downstairs, put the toddlers to bed and then let them sleep rather than waking them both to move one of them next door. (My parents did the same thing but that involved 100 feet of wire strung between three gutters).