Almost the Worst Halloween Ever

Halloween falling on a weekday confuses everyone. People aren’t sure whether they should wear costumes on Friday or Saturday, or at all. This resulted in only a few people wearing costumes while blacking out at Five Points over the weekend. Luckily, guys who didn’t dress up could claim their costume was page 37 of the Brooks Brothers fall catalogue and get away with it. The only silver lining to a weekday Halloween happened when I got a call from Dad yesterday afternoon.

“Can you come let the dogs out on Halloween? Your mother and I have a charity event to attend,” said Dad.

“Why me? What’s your daughter doing?” I asked, referring to my sister. Dad threatened to cut me out of the will if I didn’t stop referring to her in a negative manner, so now I just call her “their daughter”.

“Your sister is also hosting a charity event. She’ll be busy actually doing something for others. You should try it sometime,” Dad said in his usual tone of disappointment.

“She’s not doing anything for others. She’s just trying to make herself look charitable by putting her name on the invitation and posting a million selfies when she’s at the party. That’s ITB Charity 101, everyone knows that,” I said, trying to make her look bad.

“Just please stop by and let the dogs out. Try not to hit any trick-or-treaters with your SUV on the way over. No texting while driving. It can wait.”


“Wait, who’s handing out the candy if you aren’t going to be home?” I asked.

“No one. We just put a bowl out and use the honor system.”

“Are you crazy? Do you want your house to get vandalized? You put out an honor system bowl and your house is getting egged within 20 minutes. I’ll stay home and award the candy.”

“Award the candy?”

“I don’t “give out” candy, I’m not the government. I award candy to children who have invested time and their parents’ money into producing a good costume. That’s called capitalism.”

“Just don’t harass the children. Don’t ask them where they went to school or what their ZIP code is. I’m still getting crap from Big Caldwell after you made Little Caldwell cry last year for not knowing his ZIP code.”

“What self-respecting ITBer doesn’t know their own ZIP code? He was SIX years old!”

“Just give out the candy and don’t speak to anyone,” Dad pleaded.

“Fine. Just leave out two bowls. I’ll be over soon.”

“Two? No, do not do that ITBowl and OTBowl thing with the candy again…”

I hung up before he could finish. Of course I was going to make an ITBowl and OTBowl. How else would I reward the kids with the most ITB costumes? I got to their house and found the ridiculous honor system bowl. I grabbed a second bowl and started to sort the candy, filling the ITBowl with full size name brand candy bars, Fun-Dip and Pixy Stix (gateway candies), and money clips filled with $50 bills. I then filled the OTBowl with Good & Plenty, Bit-O-Honey, Necco Wafers, raisins, and licorice. I put the bowls on the front porch and waited.


It’s easy to spot the ITB kids on Halloween. They’ll have high-quality tailored costumes, not those cheap plastic masks that fall apart after 10 minutes. They’ll also be followed by their parents, who are sipping from bottles of Seaboard Wine’s finest Pinot Grigio and liquor drinks as they discuss financial markets and White Memorial preschool gossip. The ITB kids will use monogrammed pillowcases (Egyptian cotton, 1,500 thread count) that can hold up to 25 pounds of candy, while other kids use those small plastic pumpkin buckets that hold at most 5 pounds.

With that criteria in mind, I greeted each trick-or-treater at the door so I could judge how ITB their costumes were. I awarded the good candy for most of the evening, except when one kid showed up dressed as a Trolley Pub. I dumped a bunch of boxes of raisins in his bag and told him to never show his face in our neighborhood again. The evening was coming to a close when two kids showed up. One was dressed as Batman, and the other, well, he looked familiar.

“Nice job Batman, way to represent superheroes in the 1%,” I said to the first kid. “You…you look familiar,” I said to the second kid who was wearing Sperry’s, khaki pants, a pastel colored button down shirt and holding a bag of Fun-Dip, an iPad with ITB Insider™ pulled up, and the newest iPhone.

“I’m you. Now give me the good candy before I call my Dad,” he said.


I was speechless. He had it all. The ITB uniform, the demanding attitude, threatening to call his Dad. But the icing on the Hayes Barton Cafe cake was when he pretended to start Tweeting, “Hey @BonnerGaylord, this loser is taking forever to hand out the candy. Can we get him banished from ITB?” I dumped the entire bowl of ITB candy into his pillowcase.

“You win. Take it all,” I said, as I began to tear up. I had to go inside so the kids wouldn’t see me getting emotional. I sat on the couch thinking about the impact I had made on these children. I picked up the living room iPad that was displaying our driveway security cameras. I watched as the little WNFIV walked down the driveway, monogrammed Egyptian cotton 1,500 thread count pillowcase full of candy in tow. His friend said, “How’d you know that would work? He gave you all the candy, just like you said he would.”

Little WNIFV replied, “We’ve been neighbors for years. My parents said I should just play into his ego and he’d cave because he’s in a state of arrested development and dying for attention from anyone. The best part is I didn’t even have to dress up. This is what I wore to school today. That guy is so pathetic.”

“Wow, he’s still staying in character,” I thought to myself. I was so proud.

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