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First, take note of whether your child sleeps through the night without coming to you for comfort. If he doesn't, he may feel anxiety about staying all night at a home that is not his own, once he is there. Another sign of possible difficulty is that of elaborate bedtime routines. A child needing such care may not find such an understanding adult at the home he is visiting. The other children may also find the custom strange. The last sign to look out for is that of whether he is especially upset when you leave him. Take note of clinginess, as well. This may be a sign that your child will not do well a whole night away from you.
If your child still wets the bed, there are some precautions that can be taken. For example, your child may wear a pair of overnight briefs designed to keep your child's bed dry throughout the night. Have a trial run, where your child has a mock sleepover in the living room. As your child gains confidence, she may even wish to have her best friend over for a sleepover. Eventually, she'll feel ready and comfortable with spending all night in someone else's house. Talking with the parents who are hosting the sleepover can not only assure things go smoothly, but avoid trauma on all sides, should something go wrong.
If you and your child decide it's time for him to spend the night at a friend's house, assure him that he can call you any time he needs to and that you will pick him up. Be sure he knows to alert the parents in charge of the sleepover of his plan to leave. It would be dreadful for them to wake up the next day and think they've lost someone's child.
You can speak with your child about whether she would like for you to call her before bedtime (or perhaps if she would like to call you). This may only make her feel more homesick, but in some cases, it helps. Answer any questions she may have, and perhaps leave a comforting object (blanket, doll, or stuffed animal) with your child, as well as a picture of the family to look at if she becomes homesick.
Before you let your child stay at anyone's home, however, be sure you know the parents and their children very well. You need to be able to speak with them about very serious things before you leave your child with them. Talk about standards for what kinds of movies, video games, television, and music there will be at the sleepover. Be sure to find out whether there will be weapons in the house and whether they're kept locked away or not. Find out if there will be other adults and/or teenagers at the house during the sleepover, and if there are, reschedule it. Also, find out whether a teenager or the parents will be supervising the children the entire time they will be at the sleepover. If it will be a teenager, don't leave your child at that sleepover.
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