The Ages and Stages of Halloween

Every year as Halloween rolls around—which in retail terms means August—I can’t help but feel nostalgic for times in my life when Halloween meant much bigger things.

It was a holiday filled with possibilities. Costumes. Candy. And a hint of danger.

But now, Halloween feels like something to avoid because each time the doorbell rings, it makes our dogs crazy, and it really is a pain to have to keep getting off the couch.

And with that, I realized that Halloween essentially tracks the stages of your life. Think Shakespeare’s ages of man, only with ghouls and goblins.

First you’re a helpless baby, dressed for Halloween by your parents. For me, that meant the infamous pumpkin costume. I wore green stockings and had a little hat that was the top of the pumpkin and then a huge orange piece of cloth that Mom stuffed with newspapers to make me look more pumpkin-like. Instead I looked like what I actually was: a big little girl packed in newspapers. I crinkled every time I moved. To top it off, it was a hand-me-down. She’d made my sister wear the same costume years before.

But can you blame her? Back then, you couldn’t go to the store and just pick out a package with a readymade costume manufactured in some far-away place by poorly paid laborers. Halloween costumes required imagination and some spit and glue—and a mom who was talented with a needle and thread (and lots of newspapers).

Later on, my mother actually let me go trick-or-treating without her at the tender age of 8. Then again, I had a limited terrain to traverse. We lived behind a huge funeral parlor, so that place wasn’t giving out candy (although it would have made for a perfect Halloween spot to visit). There was a dentist office next door, and I wasn’t allowed to go to the apartment building across the street. Instead, my best friend and I got to go around the corner to about a dozen houses and come right back home.

As I hit adolescence, Halloween became less about my costume and all about the candy. Which in my case meant it was all about my weight. My mother would constantly ask, “Do you really need to eat all that candy?” She was trying to say I now looked like the pumpkin I used to dress up as.

But it was a huge milestone when I was old enough to cross the street and hit another neighborhood to trick-or-treat in, which meant a bigger haul and more candy to hoard for the next few months. Halloween was the food lover’s gift that kept on giving all the way to Thanksgiving.

The next stage was less about the candy or the costume and all about what mischief you can get away with. For some people that means being a punk (pranks involving eggs, toilet paper). For me, it meant going to my friend Susan’s neighborhood instead of mine.

My husband, who grew up in Geneva, said he didn’t have to wait for Halloween to be a punk; he was a punk all the time. But not the brightest punk. He was the kid who spray-painted his own name and phone number on a shopping center in Geneva so everyone knew who to call for a good time. Needless to say, on Halloween, his mother didn’t let him stray far.

In college, Halloween becomes how much liquor you can drink. Costumes get sexier, and the night becomes real-life riskier. My husband and his college roommates were known for their epic parties. One Halloween, they threw a party that is still considered legendary. At least 500 people showed up to their 800-square-foot house. (Do the math: That’s how many square feet per person?)

It was such a mess, they broke the plumbing and trashed the house. He dressed as the ugliest woman on the planet, and the evidence from that night includes a picture with one of his classmates who went on to become the real Wolf of Wall Street. Perhaps the Wolf’s penchant for overindulgence began that Halloween.

After my husband and I got married, we moved to Greenwich Village, which has an epic Halloween parade. Unlike my husband and his college buddies, these men really knew how to dress up as women. This was in the late ’80s, before we all knew what the letters LGBTQ stood for. Yet we knew the parade outside our apartment was a big coming-out party.

It was only after I had children that I knew why my mother bothered to dress me up. Halloween for a new parent begins with the photo-op stage. We have more pictures of Halloween when our kids were babies than any other time of their lives. There’s our son at age 1 in his lion costume, sharing a stroller with our first dog, Harpo. There’s my daughter and son dressed as Captain Hook and Snow White, in the expensive costumes my parents bought at Disney World. And there’s the annual picture of my kids, in front of the fireplace, dressed in costumes they chose themselves (hobo and cowgirl).

But the pictures just show the cute part. In reality, you work really hard to dress your child up, and then they cry and cry because it’s itchy or crinkly. You start trick-or-treating with them, holding their hand and sharing their excitement, and then one day you have to let go of their hand and hope they come home again. Talk about a holiday of faith: The words “neighborhood watch” take on new meaning for parents on Halloween.

We decided to become the “safe house” in our neighborhood for the poor parents who still had to go out with their kids. Meaning we would refill their liquor while their kids were filling their candy bags. What can I say? It takes a village.

One Halloween, we traveled to Connecticut to spend the weekend with my best friend Susan and her family. At that time she had three kids and we just had our firstborn, who was 3. We dressed him as Po from the Teletubbies and took him out with her three kids. But he didn’t know how Halloween worked. So when we encouraged little Po to go up to the first house and ring the doorbell, we watched his face go from fear to delight as the woman put candy in his little pillow case. “Candy? For me? Just for ringing the doorbell? Come on, Mom, this can’t be true!” Yet house after house, it happened.

He cried so hard when we had to leave the next day because he thought this was the only neighborhood that did this.

And then it happens. Suddenly your Po gets older and he ditches you on Halloween. Your kids start wearing provocative costumes that you prefer not to preserve in pictures (pimp, hooker). And you’re left alone, eating pizza and answering the door for other people’s children as you cry into your Chardonnay. Unless of course you’re invited to an adult Halloween party, where you get to meet up with aging pimps and hookers trying to feel young again.

Last year was a milestone because we didn’t stay home on Halloween. My daughter was traveling for a sporting event and my son was at college (where every Friday night is Halloween, he tells me). So we went out to dinner and left the light on with a trusting note by the candy bowl that said: “Just take one.” Apparently, some kid must have thought it meant, “Just take one bowl” because we never saw it again.

But there is hope. My mother-in-law and father-in-law, both in their 90s, live in a senior living community where they dress up each year and win the best costume prize (and hottest senior legs, because she’s got them).

That’s right. They’ve discovered the true spirit of Halloween: reveling in a night that rewards creativity and trust in the universe, no matter your age.