My odest starting this asking thing at about 5, she had her first sleep over (outside of my mothers) about a month before she turned 9! It was a slumber party for a friend that she has had since daycare. I got to know the mom over a course of about 6 years, started off slow since we barely saw eachother at daycare, but then in preschool and into the 3rd grade I got to like her on all the girls fields trips. Needless to say my daughter did very well there and we have since survived another sleep over at the friends house and three at our own house. This is a touchy subject, its hard on us moms to watch our kids grow and become independent of us. I think that the age of the first sleep over is based on many things, mostly your childs ability to go to sleep/bed on their own, the comfort zone you have with the family of where the sleep over will be, the maturity of your child and mostly the ability for you as a mom to survive the night =] I suggest that the first few times you child sleeps away from you that it is with family who will be more caring of your childs fears, like a practice run! The other thing that I have heard of that has worked for small children who want a sleep over is a "sleepless over" where you do all the fun of an actual sleep over, like wearing jammies with your friend and watching a movie with you blanket/pillow and those things that make a sleep over special but then going to your own home and bed at like 8/9 PM. Good luck and be blessed with all your boys - "A mom works from SON up until SON down" I was told this when I had my second son and I love it =] So so so true!