Olivia Jacobs' first sleepover started well, with plenty of playtime spent at a neighborhood friend's house. But when it was time for bed, the 6-year-old started to cry. Olivia wanted to go home.

Olivia Jacobs' first sleepover started well, with plenty of playtime spent at a neighborhood friend's house. But when it was time for bed, the 6-year-old started to cry. Olivia wanted to go home.

"She said the bed just didn't feel right," says her mom, Tracey Jacobs. By 10:30 p.m., Olivia was tucked safely in her own bed, sleeping off her first overnight attempt.

For many youngsters, the first sleepover with a friend or relative can be an unnerving experience. For others, it's fun from sunset to sunrise. Knowing when your child is ready for that first sleepover, though, can be as tricky as settling down a roomful of first graders for the night.

Yvonne Gustafson, Ph.D., parent consultant with the Elizabeth Blackwell Center, suggests parents ease into that first sleepover with a "late party," during which children stay up until 10 p.m. or so and then return to their respective homes. "Some children find it fun just to stay up past bedtime," she said.

Before Jennifer Reynolds' two oldest daughters, Julianna, 9, and Cassie, 7, spent the night with friends, "they had lots of experience staying over with their grand moms," she said.

By the time Julianna was ready for her first sleepover with a friend, she had enjoyed several play dates at the friend's house. "I already felt comfortable with the family she was staying with," Reynolds said.

Since then the girls have enjoyed a handful of sleepovers, both at home and away. Reynolds says she has never let the girls schedule a sleepover without first scheduling a play date.

Jacobs also insists on meeting and talking with parents and their children before engaging in a sleepover. A play date is a good time to establish boundaries and house rules.

"But children should be reminded of their own family rules before spending time at another family's home," Gustafson said. For example, if watching R-rated movies is forbidden at home, then the child may need reminded that it isn't acceptable at someone else's house either.

"That's where it really helps to know the other family," Gustafson advised. "If you don't trust that other adult, your child shouldn't be in that other house."

For Jacobs, feeling comfortable with a host family is more than just asking the right questions. "If I have to ask a parent those types of questions, then I don't know that parent well enough for my child to stay there without me."

Gustafson also advises talking to your child about appropriate and fun things to do with friends during a sleepover, especially if the sleepover involves more than just one friend.

And if the sleepover is at your house, the experts suggest taking an active interest in the party. For Jacobs, that typically means helping the girls with a craft project and assisting them in the kitchen while they make pizza.

"The best idea I've seen is keeping activity to a 30-minute time slot," Reynolds advised. She suggests hosting no more party goers than the age of the child.

"It also may be helpful to invite a friend of your child's sibling to sleepover to avoid any feelings of exclusion," she said. "Or, if your children are close in age, combine two parties into one."

Before the party begins, ask your child if he has any toys he does not want to share. By putting those toys away before friends arrive, tantrums and tears can be avoided. "If your child does act up, apologize to other guests and even offer to take them home," Gustafson said.

And whether you are hosting the sleepover or sending your little one on her way, be prepared for the child who either wants to stay up all night or the one who wants to come home. In the end, though, it's all about having fun.

"It's supposed to be fun for the child," Gustafson says. "It's supposed to be a learning opportunity."

The experts suggest packing these items for the sleepover suitcase:
Pajamas Comfortable play clothes that can get dirty Favorite book or magazine (older children) Toiletries Sleeping bag or other bedding. Don't forget the pillow! Medications Emergency phone numbers, especially if you will not be home during the sleepover Home phone number (younger children) or cell phone (older children) Child's "lovey" or comfort item, such as a blanket or bear (younger children) A family picture for comfort (younger children) Board games, CDs, nail polish, craft kits (older children)

Amber Stephens is a Columbus-area freelance writer and editor. She is also the mother of two young children.