February 17th, 2020

Valentines Day 1990

This post originally appeared as a series of tweets on 2/14/2020, but the thread got all weirded up, so I’m preserving it here in story form.

Thirty years ago today, I was a Senior at a small private high school. There were around 30 people in our class and roughly 95 in 9th-12th grades. So far into high school, I had dated two girls: B. (Sophomore year) and different-B. (Junior year), and those stories will be reserved for a later time (or never!). I was not dating anyone at the time of this story.

I don’t remember exactly how it came about, but a girl in our class and I did one of those “hey, since neither of us are dating, let’s be each other’s Valentines” things. All in good fun, most of our class was friendly with each other. (Let’s call her “Sherry” because it rhymes with her real name but isn’t actually her real name, so I won’t get sued here.) Sherry and her twin sister were born on the exact same date as I was, just a little earlier in the day. We jokingly called ourselves “the triplets,” which is not important to the story at all, just some more background.

So the day comes, and I went all out, because that is what I did back then:

  • a very nice card
  • flowers (pretty sure it was roses, but I don’t know how many)
  • a box of chocolates
  • I think one or two other little things (stickers or gadgets, like that)

I also dressed up. Our normal dress code mandated ties for guys, but we’d wear “casual” ties – I had a couple knit ones, a skinny leather one, that kind of thing. But for this most special day, I wore a fancy tie and a sportcoat. A sportcoat!

I show up at school all dressed up and I give these things to Sherry and she is…


What’s the right word here?

“Overwhelmed” isn’t quite right.
“Aghast” is too negative.
“Embarrassed-ish” maybe?

A mix of all of these things.

Needless to say, it’s more than she expected. Like, a lot. She proceeds to do her best to avoid me for the rest of the morning.

Our school was such that we had chapel three times a week, the whole school assembled together in one room with a stage (the Fine Arts Hall, it was called at the time, Room 306). For some reason I no longer remember, I was giving an announcement that day in chapel. I was a Senior, I was involved in a lot of things, it wasn’t terribly unusual for me to do this. When the principal said something along the lines of “and now MadMup has a special announcement” I made my way to the stage. I think he even made some sort of crack about me being all dressed up for the occasion.

So I get to the stage and happen to look over where Sherry is sitting, and she has a look of absolute terror on her face. She is wide-eyed and pale as a ghost, gripping the arms of her chair while trying to shrink back into it.

[I feel I should mention at this time that the reason I hadn’t dated much was because I was… well, I was weird. I was the geek, the sci-fi nerd, the class clown. I had friends, people liked me okay, but… no girls were falling over themselves to date me… and I do not blame a single one of them. I had a lot to figure out yet. Still do! But that’s a story for another time.]

So, yeah, Sherry is absolutely mortified and I’m confused for the briefest of moments as to why, but then it hits me: she thinks I’m going to do some sort of Valentines thing for her in front of the whole school. And, honestly, I was just the sort of person who might have done something like that. I once sang a song I wrote (to the tune of “Goober Peas”) about keeping basketball stats in front of the whole school to earn a letter in the sport (these were complicated times).

It is fortunate for all involved that I was not then the person I am now, because the me of today, upon noticing something like that, would immediately make a joke about it and cause the exact embarrassment she feared. I wouldn’t do it meanly, it would just… happen.

Instead, I just went on with my announcement, and then made my way back to my seat. Sherry was visibly relieved, and I mean, visibly. She must have been terrified. I still feel a little bad about it, 30 years later. I should have given her a heads up, I know that now. Anyway, that dispelled the awkwardness of the morning and we were able to laugh about it after chapel, where she confirmed my suspicions that, yes, she was afraid I’d had some huge gesture planned.

By St. Patrick’s Day the next month, I would be dating a girl in our class, and we would end up dating for a little over two years.

“Ah,” you say, “but there is one detail you have left out. What did Sherry do for you on that Valentines Day?” An excellent question.

She gave me little wind-up plastic heart with feet. Once wound, it would hop around for about 4 seconds. It was cute.

Thanks for tuning in! Next time on Adventures With MadMup, I’ll tell you about the time a whole cabin of girls at summer camp broke my heart.

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