My Sad and Weird and Angry Milkshake Brings All The Boys to The Yard

I was in ninth grade, sitting on a bench with a friend waiting for the first bell to ring.  The usual group of older kids walked past us from the art room over to the 600 Building, like they did every morning.  There were probably a dozen of them, all friends, boys and girls, with one couple who seemed to be attached to each other as if their limbs were going to fall off and die when they got separated from the host-body of their love.

I always took notice of the couple because she was adorable, like a smiling little elf, and her boyfriend wore one of those hats that guys wore in the early 90s, which probably resulted in a lower birth rate in the early 90s, because those hats were sexually repellent.  This one.


About four months into the school year, Hat Boy walked by one day, poured across the girlfriend as always, and leaned over and handed me an envelope and walked away.  On the outside of the envelope was written, “To the girl with the beutiful eyes”.

You have no idea how many times I just had to type that to get it to stop auto-correcting the spelling of “beautiful”.

As a professional social leper up to that point in my life, in my stretch denim skirt and turquoise mock turtleneck over my much not-sought-after chest of an anemic 10-year old fetus, I assumed he handed this envelope to me as a joke of some kind, and that if I opened it, a can of snakes would shoot into my eyeballs.

Or maybe it was a case of mistaken identity?  Either way, he was just an intermediary passing this card off on behalf of one of his dozen friends.

I opened the envelope and there was a Christmas card inside, with a cute cartoon chipmunk wearing a Santa hat on the front.  Inside the card it said:

You’re too pretty to be so sad.  I’ve never seen you smile, but I hope you will.

Have a very Merry Christmas!

From someone crazy.

Someone you don’t even know.

Okay, no case of mistaken identity there.  In walking past me every day for four months, nobody in that group had ever seen me smile?  That sounded about right.  I was conceived, gestated, born, and raised with Resting Bitch Face.  These are un-retouched progression photos of me from birth to today:


I know, it seems impossible that a person could look so permanently sad and weird and angry and not be in prison for life or at the bottom of the East River after plunging off the Brooklyn Bridge.  I know this about myself.  Sad and weird and angry is my charm.  If I were a man, you’d call it “brooding”, thereby making male-me irresistible to women with perilously low self-esteem.

And I should know.  I spent most of my dating-years being that woman.

“This guy seems sad and weird and angry!  Let’s date him and then be surprised at how sad and weird and angry he continues to be!”

I spent the rest of the school year trying to figure out which one of those guys had written this card.  It drove me crazy.  At that point in my life, most guys’ opinions of me were, “I guess she’s kinda funny?” and the notion of any of them desiring romance with me was as laughable as I thought my jokes were.  And by “most guys” I mean literally one guy named Mike.

Nothing came of it.  Their big group of friends still walked by every morning, and I had no idea who was behind this.

Four years later, I was seated at a table at Denny’s around 3am with my degenerate friends, and guess who our server was?  Hat Boy!  He took our order as if we had never seen each other before, brought us our food, and eventually the check.

As we went to leave, I found my nerve and said, “You handed me a card from a secret admirer like four years ago.  Who was it from?”

He said, “It was from me.  Why would I give you a card from someone else?”

I said, “Well, you were with your girlfriend when you handed it to me…”

He said, “And?”


23 thoughts on “My Sad and Weird and Angry Milkshake Brings All The Boys to The Yard

  1. Like, wow you spent all that time trying to figure out who the card was from and all along it was from HAT BOY!?!?! Did you ask if he was still attached at the lips to his girlfriend from high school, or was he still wearing said hat at the Denny’s and still sexual repellent?

    Liked by 1 person

    1. I had a strict dating policy at that point where if a guy wasn’t a junkie or a destructive weirdo, I just couldn’t bother to be interested. Someone with an actual job was enough repellent enough for me, even without the hat.

      Liked by 1 person

  2. Dry humping one while passing secret admirer notes to another is so uncool, but so typical. Some of us can actually outgrow that stage by late middle age or thereabouts so don’t lose hope entirely. My strategy would have been to keep telling you stupid jokes until you either cracked a smile or cracked me upside the head. Either way the acknowledgement would have been welcome. Was Hat Boy still wearing his hat?

    Liked by 1 person

  3. That was sweet… right up until the end. Shame your secret admirer had to be a dick.
    That being said I’m glad I was old enough to be married in the early 90’s because that hat would have put me off sex for years…
    WT utter F?

    Liked by 1 person

  4. I need like at LEAST 3 more chapters of this story! It was so good! What the hell was he thinking though? I have to know! Was everything he wrote just totally childlike honest curiosity? Or did he want to bang you? Like how was he crazy? So mysterious with the “you don’t even know” part,lol! Gawd middle school what such a freaking mess,lol! GREAT writing though.👏🏻👏🏻👏🏻

    Liked by 1 person

    1. The confidence he displayed while wearing that hat gave me the impression he thought he was some kind of Casanova. If he weren’t trying to get me to be his 9th grade mistress, I would almost admire his boldness! 🤣

      Liked by 1 person

  5. Oh the 90’s. High school boys and the 90’s. Yikes! I told my high school crush in the late 80’s (who did not give me the time of day) to ‘Get out of my dreams and get into my car.’ I cannot remember if I wrote it in a note or spoke the words to him. No idea – absolutely none – why I never dated in high school.

    Liked by 1 person

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