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The hardest part of leaving your toddler with a baby-sitter or a caregiver will always be saying good-bye. To make it little easier, try the following:

Get ready in advance, when possible, so you can spend time together before you separate. If your pass the last half hour before the baby-sitter arrives getting showered and dressed, your toddler may feel neglected while you’re still home, and abandoned once you’ve left. Also try to avoid rushing around frantically at the last minute. This will not only leave you feeling frazzled but could transmit a sense of anxiety and upheaval to your toddler. At least fifteen minutes before you leave, sit down with your child and read a story, so a puzzle, or build a house with blocks. If you simply don’t have the time to get ready in advance, get ready together. Set out some toys or dress-up clothes for your toddler to play while you dry your hair and put on clothes.

• Get your toddler busy before you get going. Set up an engaging activity which your toddler and the baby-sitter can enjoy doing together. Taking this approach may not keep your toddler from crying when you leave, but it will give them something to go back to once you’re gone.
• Leave your toddler with a reminder of you. Whether it’s your pillow, your afghan, a snapshot of you in a Lucite frame or a lipstick-print kiss on the back of the hand, having a little something of yours to keep close may help your toddler deal with the separation. However, if the babysitter reports that the reminder seems to make your toddler miss you more, skip it.
• Leave the dramatic farewell scenes to the movies. Keep your exit casual. If you’re harboring feelings of apprehension or guilt, keep them well-hidden. As briefly as possible, explain to your child that you are going out and that you’ll be back soon – try to use the same lines you used on practice outings to the next room. Promise a favorite activity when you return, if she’ll still be awake (“When I get home, we can read a book”) or for the next morning, if she won’t be, and plan to keep that promise. Choose a light parting phrase on your way out (“See you later, alligator,” is a favorite; eventually, you can teach your toddler to respond, “After a while, crocodile”), and use it every time you leave the house.
• Have your toddler wave you on your way. If there’s a window in your home that faces the street, the driveway, or the parking lot you’ll be leaving from, have the baby-sitter take your toddler to it so they can wave good bye. Even if there’s a lot of sobbing with the waving or your child refuses to wave at all, smile convincingly, wave enthusiastically, and leave.
• Arrange for your child and the baby-sitter to leave with you, when feasible. Sometimes that’s easier for a toddler. If your baby-sitter takes your toddler to the park or to a play date at a friend’s house, and they leave the house with you, your child may not feel so deserted. Be sure to make it clear that you’re going out, too. Otherwise, should they get home ahead of you; your toddler may be shocked to find that you’re not there. What’s more, she may become reluctant to leave the house without you in the future.