I'm not sure whom to leave him with.
The better your kid knows his caregiver, the smoother his sleepover will be. "Grandma or Auntie or his regular nanny is always better than bringing in a new babysitter," says Fran Walfish, Psy.D., author of The Self-Aware Parent. So if your baby hasn't spent much time with a sitter, test the waters with date nights before you try for an overnighter. When you're ready to leave your little one for the night, persuade the sitter to come to you rather than leaving him at her house, suggests Dr. Walfish. Familiar surroundings will make your child feel more secure.
I want the sitter to do it my way.
For her first weekend getaway without 14-week-old Sophie, Nikki Boone, of Middletown, Delaware, made sure her father- and mother-in-law were prepared: "I sent them e-mails with instructions for picking Sophie up from her child-care center and about her feeding schedule. I also posted her schedule on our fridge." It's smart to pass along info about your baby's likes, dislikes, and daily activities; if she can stay on routine it'll be less stressful, says Dr. Wider. But remember that it's not the end of the world if your sitter does things differently than you would.