rites of passage

First day of school? First night with a new sitter? First flushed goldfish? Here's how to manage 10 stress-prone milestones. (R.I.P., Swimmy.)

Sure, there are those purely blissful firsts, the ones that get a full page in the baby book, immortalized in home videos--tweeted about, even. But there are also the angst-ridden instances that come with a hefty dose of how-the-heck-do-we-handle-this head scratching and plenty of tears (rushing to the ER, say). Deep breath. Here's how to take these situations in stride so your kids can, too.

the first...day of kindergarten

how to handle it: "The kids who tend to do best are those who have come to school beforehand and familiarized themselves with the teacher and the classroom," says Louise Lang, who has taught kindergarten or first grade in Huntington, New York, for 25 years. Call your school district's office to learn about orientation, which is typically held the spring before school starts; often a "practice" bus ride is included. And get your child excited: Read going-to-kindergarten books; point at buses going by. Then give it some time. "This is a big adjustment for kids, and some may take until December before they feel completely comfortable," says Lang.

and for heaven's sake, do not: Pull a Steven Spielberg. "I once had a dad follow the bus with his video camera the entire way to school. Then he filmed the kid getting off the bus, walking down to the classroom, hanging up his coat," says Lang, who also had a parent who hid in the bushes and peeked in the classroom windows. Besides being embarrassing for the child, creating too much of a fuss will add to the anxiety he might already feel.

the first...sibling

how to handle it: Get the child eager to meet the new baby before she gets there, says Michelle Duggar, a Springdale, Arkansas, mom who knows a thing or two about welcoming a new addition into the family (she's the mother of 18; see for yourself in the TLC reality series 18 Kids and Counting). "I let them talk to my belly and tell them the baby can hear them," says Duggar.

With all that buildup, you have to be careful when the baby comes home, as kids tend to be aggressive with their attention. Duggar has her children practice holding their dolls and teaches them to kiss on the back of the head and be gentle. Even with this training, have someone stand guard. "Without fail, the 16-month-old wants to touch the baby's eyes," says Duggar. Finally, says Dawn Huebner, Ph.D., a child psychologist in Exeter, New Hampshire, and a coauthor of the children's book What to Do When You Worry Too Much (Magination Press, $16), keep as much the same as possible: "If there is to be a bed change or a room change, have it happen in advance of the baby's arrival."

and for heaven's sake, do not: Forget to carve out quality time with the eldest child. While it's always great to look for opportunities for him to be the big helper, give him one-on-one time, too.

the first...crush

how to handle it: Talk about it. "The first crush is a good opportunity to start discussing what your child likes about different people, what qualities attract her to one person over another," says D'Arcy Lyness, Ph.D., a child psychologist for KidsHealth.org. Of course, she will probably be on to Chris or Will by week's end, but if she's having a tough time getting over Timmy, share your own first-crush experience. "Tell her it's something we all go through," says Lyness. For insight into what the first-crush experience might be like for your child, add Little Manhattan, a kid-friendly 2005 film about an 11-year-old falling in love for the first time, to your Netflix queue.

and for heaven's sake, do not: Make a joke of it. No matter how cute/ridiculous/silly you think your child's swooning is, don't let it show. "Try to tread that nice middle ground between not taking things too seriously and dwelling on it too much," says Lyness.

the first...trip to the ER

how to handle it: Call your child's regular doctor immediately, before taking her to the ER, says Mary Ellen Renna, a pediatrician in Woodbury, New York, and the author of Medical Truths Revealed! (Select Books, $15). "Your pediatrician may be able to help you interpret test results, expedite waiting time, and speak to the doctors about preexisting conditions while you're waiting in the ER," she says. As for preparing the child, less is more. If it's an X-ray, tell her someone is going to take a picture of her; for an IV, say there will be a pinch and then the medicine will go right in to make her feel better. "The number one thing kids want to know when I send them to the ER is 'Will Mommy be with me the whole time?' " says Renna. And the answer is yes. Apart from X-rays, there is almost no time a parent has to leave a child alone in the ER. You can tell older kids more: "At 10 years old, their fantasy of what the ER is like is scarier than the reality, so details help," says Renna. Reassure a child that even if he has to stay overnight, you'll be there the whole time (in one of those comfortable bedside chairs). Try to bring something from home (a blanket, a toy) to make the child feel safe.

and for heaven's sake, do not: Avoid talking about it after the fact. "You don't want children to be afraid of the doctor going forward," says Renna. Besides, kids are usually eager to recap their hospital adventures.

the first...big loss in sports

how to handle it: The key is to focus on the performance (complimenting your child on a great play, for example), not the outcome. "Be sympathetic, let your child express his disappointment, then remind him that sports are about socializing and having fun, not just winning," says Brooke de Lench, the founder of MomsTeam.com, an online resource for youth-sports parents, and the author of Home Team Advantage: The Critical Role of Mothers in Youth Sports (Collins Living, $15). But let's be honest--who wants to be a loser? "I'm not one to sit there and say, 'It's totally fine to get beat all the time,' " says Drew Brees, quarterback for the New Orleans Saints, who admits to some post-game tears in his youth-sports days. "I think it's good for kids to get upset when they lose." But once they've cooled off, they should learn from it, too. "Pull them aside and say, 'Do you know what you would do differently in the future?' Ask them to say it rather than telling them," says Brees, a three-time Pro-Bowl pick and a new dad who plans to coach Little League some day.

and for heaven's sake, do not: Hurl your hat into the stands or kick dirt at the ump. "A child's reaction tends to be directly proportional to the parents'," says de Lench.

the first...bad grade

how to handle it: "Kids will be more open to talking about the grade if you sympathize first with their embarrassment or anger," says Huebner. Give your child time to react on her own, then ask questions to help her figure out what happened. Did she not understand the work? Did she make careless mistakes? "Stay as nonjudgmental as possible, even if you know the F is her fault," says Huebner. Then talk about how to correct the problem in the future. Sharing one of your own failures (a bad grade, a bad performance review) and how you coped can help her move on.

and for heaven's sake, do not: Lose perspective. "One bad grade is one bad grade," says Huebner. "It doesn't mean your child is going to fail the class, so encourage her to let it go."

the first...experience with death

how to handle it: Children learn to grieve by watching you grieve, says Kate Atwood, the founder of Kate's Club, an Atlanta-based organization for children who have lost a parent or a sibling, and the author of A Healing Place: Help Your Child Find Hope and Happiness After the Loss of a Loved One (Perigee Trade, $15). It's OK to let them see you express your feelings and to involve them, in an age-appropriate way, in the rituals of commemorating the deceased. "It helps to give them closure," she says. Other tips:

* Talk about the person who died in the weeks and months following his or her death. "Kids recognize their parents' sadness and often stop talking about the loved one in an attempt to keep the sadness away," says Huebner. Creating a scrapbook of photos and happy memories is one therapeutic activity. And be sure to let your kids know that it's OK to not feel sad all the time.

* Offer reassurance. "When someone dies, kids often become fearful that others will die, too," says Huebner. "Talk about the death as unique. 'Grandma had a special kind of sickness different from the way we usually get sick,' for example."

* Finally, if it's a pet that has died, don't rush out to replace it. "While it's fine to eventually buy another dog, encourage your child to give it a different name and to recognize it as a totally different animal--not Fido II," says Huebner.

and for heaven's sake, do not: Confuse your children by using vague language. "Say 'dead,' not 'lost,' 'gone to sleep,' or some other euphemism," says Huebner.

the first...sleepover

how to handle it: Find out what's planned so you can walk your child through what to expect. It's also good to let him know he might be nervous or miss you. "Some parents skip this step, as they don't want to trigger their child's fear, but it actually helps more to talk about nervousness in a way that normalizes it," says Huebner. Then give the child ideas for how to deal with it. Some kids might want to bring their own pillows--or your pillow. Let them know it's OK to call you to check in, especially before going to sleep.

and for heaven's sake, do not: Dwell on what went wrong if you get a come-pick-me-up phone call. "Discuss the fun parts of the sleepover," says Lyness.

the first...night with a new babysitter

how to handle it: You know how excited you are to be going out for a change? Make your child that pumped up to be staying in. Introduce the babysitter before the big night, then plan something fun for your child that evening. For example, fix his favorite dinner, buy cool snacks, or rent a movie that he's dying to see (or the one he's watched 25 times that he's still dying to see). It's also good to tell him where you're going and when you'll be back.

and for heaven's sake, do not: Forget to check in periodically to remind your child that you've still got your eye on him and that you're OK. "Some kids worry about their parents when they're not home, so when they hear from you and know that you're having a good time, that reassures them," says Lyness.

the first...lost tooth

how to handle it: Anxieties can soar around this experience. The dangling! The blood! "Some kids think the tooth might be attached to something important, something they need," says Dustin James, a pediatric dentist in Wilsonville, Oregon, who sees about 70 sets of mini teeth a day. At your child's regular dental appointment (before she starts losing teeth), ask your dentist to explain to her exactly what's going to happen and what it will feel like and why. James shows his patients X-rays so that they can see how the new teeth are trying to come in. Then get the child psyched for the Tooth Fairy. Go to Officeofthetoothfairy.com for incredibly official-seeming Tooth Fairy swag, then check out Oeuf's adorable molar-shaped pillow with a pocket for the tooth at Oeufnyc.com. "This can be one of the most exciting things for a kid," says James. "When I tell patients they're about to have a loose tooth, their faces light up."

and for heaven's sake, do not: Get impatient. "Parents usually worry more than the kids about why the teeth haven't loosened up yet and when they can expect them to." This can happen as early as five years old and as late as seven. It's best to let the teeth come out on their own, says James.

read all about it

Real Simple's experts agree that scenario-specific books can be a great way to guide a child through first-time experiences and feelings. Here are some of their favorites.

The Kissing Hand, by Audrey Penn

(Tanglewood Press, $17)

Good for: Reassuring your child that you're thinking of him when he heads off to school that first day--and giving him a trick (placing his mom-kissed palm to his cheek) for times he misses you.

The Tenth Good Thing About Barney, by Judith Viorst

(Simon & Schuster Children's Publishing, $16)

Good for: Helping children focus on the happy times with their deceased pets and teaching them that everyone has a different idea of heaven.

How to Be a Baby... By Me, The Big Sister, by Sally Lloyd-Jones

(Random House Children's Books, $16)

Good for: Previewing the feeding, diapering, crying, and cooing that come with a new baby--and just how special it is to be the older (wiser!) sibling.

Sam Is Not a Loser, by Thierry Robberecht

(Clarion Books, $12)

Good for: Teaching sportsmanship in different game situations and showing kids that playing and not winning is more fun than never playing at all.

When Dinosaurs Die: A Guide to Understanding Death, by Laurie Krasny Brown and Marc Brown

(Little, Brown Books for Young Readers, $8)

Good for: Explaining why someone dies, the rituals that might take place, and pretty much everything else there is to know about death.

The Berenstain Bears and the Sitter, by Stan and Jan Berenstain

(Random House Children's Books, $4)

Good for: Revealing just how much fun a night with a new baby-sitter can be, even if she seems really scary at first.

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tip

For a complete insider's guide to the emergency room, including questions to ask the doctor before you leave, go to realsimple.com/emergencyroom.

Got old love letters in the attic? What about an awkward photo of you, shortest kid on the basketball team? Tangible evidence that Mom or Dad hit tough times will cheer up a bummed-out kid.