While most little girls see the megillah reading as an opportunity to bust out the Disney Princess garb, there are always a handful who get a kick out of being Haman, the way I did. But on Purim this year, which arrives Saturday night, there are likely to be very few, if any, little boys dressed as Esther.

Why? Because when little girls dress “boyishly,” everyone thinks it’s cute. I adored putting baby Josie and baby Maxie in Osh-Kosh engineer overalls and teensy black Converse high tops. If I’d had sons, would I have put them in pink onesies and glittery parachute pants?

Yet many parents do have what Sarah Hoffman, a Jewish writer who blogs pseudonymously, calls “Pink Boys.” (It’s the title of her forthcoming book). Whether a kid is growing up in Berkeleyest Berkeley, Calif., or in Hasidic Williamsburg, Brooklyn, the urge to be fabulous isn’t something entirely within the parents’ control. “Gender identity isn’t something we just impose on kids and expect them to suck it up, like eating vegetables or going to school,” Hoffman writes. “It’s part of who they are, whether that satisfies us as parents or not.” Sometimes, little boys who love dresses grow up to be gay. Sometimes they’re transgender. And sometimes a pretty dress is just a pretty dress. Parents needn’t jump to any assumptions about what a little boy’s love of tulle means, but they should listen to and respect the individual child’s desires.

“Don’t get ahead of yourself,” said Julie Holland, an assistant professor of psychiatry at the NYU School of Medicine. “The important thing is not to induce shame in your kid. It’s essential that kids feel they are OK, that they are loved and lovable.” She offered advice to parents whose sons want to wear dresses to school. “You can say, ‘In our culture, many people think that only girls should like pink, and that’s kind of silly. They think some toys and outfits are ‘boyish’ and some are ‘girlish.’ How do you think people will respond if you wear the dress to school?”

The trick is balancing your child’s safety with his or her self-expression. You have to find this balance without letting your own gender-issue mishegas get in the way and without making your kid feel judged and wrong. If your child’s teacher is supportive, the school is a nurturing place, and your son’s passion for silk charmeuse is implacable, why not let the kid wear a freakin’ dress? The issue, of course, is if the school environment isn’t supportive. “You don’t want to hurt him, and you don’t want the world to hurt him,” said Holland. “Which means the ultimate solution is to change the world, not your kid.”

That means if your kid really wants to wear dresses, you find allies within the school community to protect your child. If the kid is experiencing regular bullying, it may mean finding another school or homeschooling. “The path isn’t easy,” Holland added. “But your job as a parent is to, as much as you can, create a safe space for your kid.”

There has conveniently been a boomlet in children’s books about boys in dresses. I can think of four books published in the last year alone that address this issue. 10,000 Dresses, by Marcus Ewert, gorgeously illustrated by Rex Ray, is the story of a child named Bailey who looks like a boy but knows she is a girl inside. She dreams of wearing brilliant dresses made of crystals, rainbows, flowers, and windows, but her family refuses to acknowledge her true self. Ultimately she does find a supportive friend. Unfortunately, I think this book would baffle most little kids: Its use of pronouns is very confusing for kids who view the world in binary ways—the omniscient narrator assumes that the reader understands that Bailey is a she, despite looking like a he, but most kids won’t make that leap. The pictures are gorgeous, though, and I can see older children who are already familiar with transgender issues really loving the book. (Also fun: the blurb by fashion-designing Jew Isaac Mizrahi: “I love this book! If I had read it growing up, I might have felt better about my dress-wearing habit!”)

Then there’s Be Who You Are by Jennifer Carr, illustrated by Ben Rumback, a picture book based on the author’s own parenting experience raising a transgender child. And My Princess Boy by Cheryl Kilodavis, illustrated by Suzanne DeSimone, the story of a little boy named Dyson who likes to wear a tiara sometimes and jeans sometimes. Kids may be turned off by the illustrations, depicting people without faces (each character has a blank oval where the face should be, perhaps so everyone can project herself into the tale, but I think it just looks creepy). The book, by a mom who had a harder time than Carr in coming to terms with her child’s identity, pleads:

If you see a Princess Boy…
Will you laugh at him?
Will you call him a name?
Will you play with him?
Will you like him for who he is?

The one middle-grade novel in the bunch is The Boy in the Dress by David Walliams, a comedian who I am told is super-famous in England. The sweet, stylish spot illustrations are by Quentin Blake. The main character, 12-year-old Dennis, is a soccer-mad boy who loves to read Vogue and gradually admits to himself that he wants to wear dresses. The most popular, most gorgeous girl in school, on whom Dennis has a crush, befriends him and encourages him. There’s a lot of goofy, broad physical comedy (very British) and an ending that was, for me, too unrealistically rosy. But Josie, my 9-year-old, went crazy for the book, reading it over and over. I realized that for Jo, a child with an acute awareness of injustice, the book was a perfect fairy tale. She loved the ending precisely because it would never happen in the real world. What I saw as weakness she saw as wonderful.

Alternatively, as you consider the issue of dressing up—or cross-dressing-up—this Purim, you could always turn to our sages for advice. Deuteronomy may include a prohibition against a man wearing women’s clothes, but Rashi wrote that this kind of dress is wrong only when it leads to adultery, and Maimonides added that cross-dressing is wrong when it is for the purpose of idol worship. To these wise rabbis, the prohibition is against cross-dressing in order to do harm. If harm’s not the goal, as Rabbi Elliot Kukla and Reuben Zellman point out, quoting the Babylonian Talmud: “v’ein kan toevah”—there is no abomination here.

Will the world become more tolerant of boys in dresses? Holland offered a surprising analogy. “Until recently, peanut allergy wasn’t taken seriously,” she said. “Now every school has a policy, and everyone accommodates it. But parents had to educate people about the special needs of their sensitive kids. I’m not comparing cross-dressing to allergies. I’m just saying with education, change is possible.” And maybe that means one day we’ll see a lot more little boy Esthers.

Was Max an observant Jew like his writer cousin? “We do not have good information on ‘how Jewish’ Max was,” Lipner told me. “But his welcoming hundreds of thousands of people onto the farm strikes me as a rather extraordinary example of the Jewish value of hachnassat orchim—welcoming guests.” Max Said Yes! isn’t an explicitly Jewish book, and it doesn’t draw an overt parallel between Max’s behavior and that of our tent-opening forefather Abraham, but the authors believe the analogy’s there. Still, is it weird to have a book about Woodstock that doesn’t mention sex or drugs at all? Lipner and Yasgur told me they’d joked around with some couplets that were left on the cutting-room floor:

In land filled with alfalfa seed
They relished LSD and weed.
They lay down in the fields and went to bed
With people to whom they were not wed

Mm, not so much. Ultimately, the authors decided that parents could use the book as a jumping-off point to talk about sex and drugs with their kids—or not. So for those of us—Woodstock Generation, Gen X, and Millennials—who did inhale, the question remains: how do we talk about drugs with our kids?

Kiki Schaffer, a social worker and director of parenting, family and early childhood at the 14th Street Y in Manhattan, laughs: “This subject is to parents of teens what sleep is to parents of newborns.” In other words: it’s the biggie, the giant bong in the room. Schaffer’s strategy is to plant the seed (as it were) early. “I tell younger kids, ‘Think about what we put in our body,’” she says. “Would you put worms in there?’” Schaffer believes that early education about drugs and alcohol is about encouraging kids to think about choices and self-regulation, so that when they grow older, they’ll continue to question what they ingest. As they reach preteen and teen years, she says, “Parents can start saying, ‘There are a lot of things we once didn’t think were harmful but studies have since shown they were: cigarettes, medications women were given in pregnancy.” Like many experts, Schaffer is not a fan of “Just Say No” education. “I hate it,” she says. “It doesn’t engage the hearts and minds of children or empower them to make good decisions—real life is about learning to be a decision-maker.” Indeed, those of us who grew up with Reefer Madness-style education learned only to laugh at parental paranoia.

Julie Holland, an assistant professor of psychiatry at NYU School of Medicine and author of the forthcoming Weekends at Bellevue: Nine Years on the Night Shift at the Psych ER (Bantam, October 2009), agrees that the “Just Say No” approach is misguided. For one thing, she says, recent studies indicate that marijuana isn’t a gateway drug—hysterically insisting to your kids that one toke is a fast track to Cobainville makes you look like an untrustworthy doofus. In 2008, 43 percent of 12th graders reported trying marijuana once or more—clearly they haven’t all become raving, heroin-shooting, paint-huffing street addicts. A better strategy, Holland says, is to stress the potential consequences of doing something illegal. “Many schools have random drug tests,” she says, “and if you test positive, you can’t do sports. If you’re a senior, you could lose your student loans.” Explaining how drugs affect developing brains is also vital, she continues. “Because the adolescent brain is still in a formulation stage—pathways are getting laid down, connections are being made—in a perfect world kids wouldn’t use any substances, including alcohol. But in the real world, statistics show that’s unlikely.”

Holland stresses that parents should be as concerned about legal drugs (cigarettes, alcohol, and prescription drugs) as about street drugs. Unlike the kids at Woodstock, kids today rarely experiment with acid. Today, the big drug of choice is “pharmies.”

“Excuse me?” I say, like the old fart I am.

“‘Pharmies’ are what kids today call prescription drugs,” Holland explains. “So keep track of what’s in your medicine cabinet—especially all you neurotic Jews taking benzodiazepines [Xanax, Valium] so you can sleep.” Other modern-kid faves include narcotic pain killers (Vicodin, Percocet, Oxycontin), ADHD drugs (some kids resell them as weight-loss aids), steroids, and the cough suppressant dextromethorphan (which the kids call “Robo”). Not to harsh your mellow or anything.

So, my fellow post-Woodstockians, what should we do? There are terrific online models of nuanced, non-scare-tactic-y speeches to give to teenagers. With my own kids (now seven and four), my inclination is to wait until they start asking questions. But I also don’t want to end up in the same situation as my mom, when she tried to give me the sex-ed talk long after that particular train had left the station. So in a couple of years, I think I’ll sit Josie down and say, “You may start having kids offering you drugs to feel good—pills, things to drink, things to sniff, and things to smoke. My hope is that you’ll talk to me about it. Just because something is legal doesn’t mean it’s safe. You don’t know who got what where. And if you ever get in a situation where you feel unsafe or out of control, know that you can call me or text me and I will help you or get you, no questions asked and no punishment given.”

And what if Josie or Maxie ask about Mommy’s drug history? Well, I’ll tell the truth. (And no, I’m not telling you.) And we’ll continue to share a regular sip of Shabbat wine. One recent study found that kids who drank with their parents were less prone to binge drinking. Thus in the spirit of Woodstock, I offer my own conclusion:

Your kids’ addiction you will head off
If you think of Max, and share a quaff.
Treat your kids like sensate beings.
And they’ll grow into responsible teens.

Or so I hope.