I posted a version of this story last year and you all got so much joy from my pain….I thought it was worth sharing again. And I have a little update too….

It’s true. I’m a mama who love to dress up. I love fashion and I love being “festive” and dressing up in general. Like this:

 

And even this:

As a result, Halloween has always been one of my favorite times of year. When I found out I was having a little boy, I was so excited when about all the dress-up, play time possibilities. I had visions of making him superhero capes…astronaut outfits…cool pirate get ups. The works! Yet life clearly has a sense of humor, because I was blessed with the world’s most adorable child…who hated costumes. He’s an impossibly good natured boy, who is so easy going 99% of the time—he happily wears any regular outfit I put him in. Except, of course, when that outfit might involve a character.

It all began with Wolfie’s strict NO HATS policy as a baby. Wait, no hats? What what? He’s a baby! How can he hate hats? Trust me.

When Wolfie was one, I bought a little prefab puppy dog outfit for Halloween. But because that seemed just a tad boring on it’s own, I had Greg dress up like a Westminster Dog Show handler—with Wolfie as his prize-winning pooch! Since Wolfie was still so little and liked to be carried around, they made an awesome pair.

Except my sad little pup refused to wear the “hood” that had the puppy head on it. Too much like a hat, of course.

At least I managed to sneakily draw a little nose and whiskers on him and he still looked pretty adorable.

The next year I got him the cutest little cowboy outfit…it came with wee chaps, a cowboy shirt and a super cute lil vest. I didn’t even try and add a cowboy hat, but I figured this outfit was pretty much like regular clothes. Easy peasy, right? WRONG. What I neglected to remember was that Wolfie is a very proper little man and he liked his jackets and hoodies closed or zipped up. And a vest? Well it’s like a perpetually “open” jacket. Yeah the vest? He didn’t like it ONE BIT.

He threw himself on the ground like a cartoon character, sobbing. Keep in mind that normally Wolfie is the sweetest, most low-drama kiddo around. Greg and I looked at each other half laughing and half shaking our heads….like “Really? You’re going to throw yourself on the ground over a VEST?” Thankfully he gets over things pretty quickly and once the offending vest was removed, he was all sunshine again.

The next year I had a great plan….and seemingly Wolfie-proof! Greg and I would go as Mr. & Mrs. Frankenstein—and Wolfie? He would be the Crazy Mad Scientist. Genius, right? All he’d have to do was wear a wee little lab coat (buttoned all the way up, of course) and make his hair all crazy. It was the perfect plan. Greg looked great.

I even left Wolfie help me put on my “spooky” eye make up so he wouldn’t be scared—this was a huge success.

But when it came time for his own costume, well…once again, you can see how Wolfie felt about all this:

I explained to him that Halloween was all about dressing up, and if he didn’t like the Mad Scientist outfit he could really be anything he wanted to. After some thought he declared. “I wanna be a punkin.” I was a little floored. “Um…..a pumpkin?” “Yes. Punkin, mama.” My costume-adverse child goes and picks the roundest, poofiest costume around?? “Wolfie, you know a pumpkin is very round, right? Are you sure you want to be a pumpkin?” “YES. PUNKIN.” OK. So I have to admit that I was totally a terrible mom and thought this was a lame costume idea (I know, I KNOW), but I wanted him to be happy, so a pumpkin it was. I searched high and low for a non-poofy pumpkin costume and FINALLY found one (it ain’t easy, folks). I came home triumphant. YES! Wolfie will be so excited! Except……

Oy! I can’t lie. It became a Battle Royale. He was going to wear that freakin’ pumpkin costume if it killed me. I finally calmed him down and like all savvy moms…..I negotiated a bribe. “Listen. If you wear the costume, I’ll give you something. Something good.” His ears perked up. “What?” he sniffled. “Um…you can have some chips.” Yes. I know. Bribing with snacks. What can I say? I was desperate. And Wolfie’s a salty boy, so this worked better than the promise of chocolate. With a sigh, he was resigned to his fate:

The final verdict: “I’ll wear it. But I won’t like it.”

By the next day (which was actually Halloween) he had a miraculous change of heart and happily wore Ze Pumpkin. Hallelujah!

Oh my silly little Wolfie. I’m happy to report the last two years were amazingly struggle free and he has decided costumes (and HATS!) are A-OK. His friend Emmy got him into Pokemon and decided he wanted to be Pikachu. Not only did he wear the outfit, he wore the kooky hat dealie too! Whooo hoo! It was a cheap-ass flamable costume, but HE WAS WEARING A COSTUME. Listen, I’ll take what I can get. And apparently this is a rather “rare” costume, and he got lots of props from the big kids who all shouted at him, “We chose YOU Pikachu!” He was beaming.

The next year he continued the Pokemon theme and dressed up as Ash, Pikachu’s owner.

And this year? Well, once again little Wolfie has rocked my world. He informed me that he was thinking of being Harry Potter……or a meatball. Yep, you heard right. A MEAT BALL. And folks, I’m pleased to report that the meatball won. He and Greg have been working on a paper mache proto type and I’m in charge helping with the noodle hat. Oh this boy of mine…