Messing Up My Very First Real Valentine’s Day Opportunity

Valentine’s Day always had a big build-up when and where I grew up. In the 1960’s, I was forced to participate in all of those school parties for Valentine’s Day that were obligatory in the classrooms around the country. Remember them? You would buy those cheap paper valentines and address them, and then in your classroom, use a cardboard box with a construction paper heart on it for a mailbox to hold them all. Classmates would stuff it with valentines for other classmates. In those days, before the “self-esteem” of children was a concern, and became something to build in young children, no fairness was mandated. It was rare for children to be encouraged to write one to every classmate, so of course, the popular kids made out like a bandit, and those of us in other less popular tiers, suffered some mortification depending on the haul in the mail delivery. If you were shrewd and you did not want to show a paltry number, you could quickly shove them in your desk and pretend Valentine’s Day did not matter at all.

I guess we all survived some Valentine’s Day humiliation, but I was also a born romanticist and looked forward to having a real Valentine one day. I looked forward to someday receiving that holy grail of a heart-shaped box of chocolates that I stared at in stores wondering who the lucky recipients would be.

Through elementary school I had a few crushes, unrequited; and I was also the subject of a few crushes that I did not reciprocate, but I had nothing in the way of a real Valentine on that special day through those years. Although it took me a long while (forever) to blossom, I always had my share of boys with crushes on me and even had some very temporary boyfriends from a young age. But darn it, these temporary boyfriends never seemed to happen on Valentine’s Day.

This particular Valentine’s Day memory I am writing about today came flooding back to me while reminiscing with someone about the great times hanging out in the neighborhood where I babysat through 8th and 9th grades as a “mother’s helper.” I was only fourteen years old, but back in this era, it was common for girls to start dating while in middle school at thirteen or fourteen. Lots of my peers had boyfriends. It sounds ridiculously young now, but we courted and dated in an old fashioned way, so it was okay to start so young. Remember those early Beatles songs such as “I Want to Hold Your Hand?” We were innocents back then.

Back to my memory, I was in the ninth grade, age fourteen, and I felt so gawky and awkward, just beginning in the throes of a late puberty. I wore glasses; (at a time when glasses were NOT cool to have) and for an extra attractive look, I had those big metal braces in my mouth. (The original braces of thick silver bands that wrapped all the way around your entire tooth that was the opposite of the delicate glue-on braces worn today. The term “metal-mouth” was deadly accurate with this kind of brace-work.)
Despite the horrific details above, I am surmising that I was just a little bit cute because boys seemed to like me. I was a big flirt too – an innate and early skill. Still, I had never gotten a real Valentine’s card, or that coveted heart-shaped box of chocolates from anyone and was still awaiting a real Valentine.

In this year of 1969, I was working every weekend in a different affluent neighborhood, sleeping over from Friday until Sunday working as a mother’s helper. Because I was there each and every weekend my only social life on weekends involved hanging out with kids in this neighborhood that was not my own – there was a whole different set of kids who did not go to my school. I had a bunch of free time each weekend when the parents were around, and I will never forget the friendliness of the kids in that affluent neighborhood who always let the visiting stranger tag along. In the winter, I even went sledding with them. It was a great bunch of guys and girls in this neighborhood and they never treated me like an outsider. I felt privileged to have an extra set of new friends.

One of the guys of this group who befriended me lived on the same cul-de-sac street as my employers. We were simply friends, hanging out together, talking about music that we both loved – the usual hang out and friendship stuff. I remember him as a very tall, dirty-blonde-haired boy, who also wore glasses, and maybe he had a few pimples. (I think he looked a bit like Chad Stuart of the singing duo “Chad and Jeremy” of that era). He was sweet and friendly and his name was Paul, but I had a crush on his friend in the neighborhood, a guy named Jay. Here is a photo of Chad Stuart, and this is pretty much what Paul looked like only he had smaller glasses.

Valentine’s Day fell on a wintry Friday in that year 1969. I arrived early evening for my weekend work as a mother’s helper, all dressed up for the holiday from celebrating at school. In a look I vividly remember to this day, I wore red velvet pants and a frilly white blouse, my hair in braids and ribbons, and had shiny lip gloss on my lips. I have no clue as to why I stayed dressed up just to babysit, but it was Valentine’s Day and I guess I was an optimistic teen; perhaps I was hoping to get a sighting from my crush Jay on that night even though he barely knew I was alive.

The parents of my babysitting charges of course went out for the evening, and I was left to babysit with the children alone in the house. That’s when the tall blonde haired boy Paul came over and rang the doorbell. His arms were full of goodies – he went all out for me. He brought me a giant card and other cards, and a big box of chocolates; my very first heart-shaped box of chocolates from a boy. He awkwardly asked me to be his Valentine. It was a bitterly cold night in 1969, and he was outside shivering with his array of sweet presents and a hopeful look on his face. I stood on the inside all dressed up for the holiday, with my little shining glossed lips and hair ribbons, and he must have momentarily thought he was in luck.

I was so astounded with how sweet, but how misdirected his romantic advances were, that impulsively I grabbed everything from him and slammed the door in his face. It was a momentary reaction from my shock. He was the WRONG Valentine!

Replaying our interactions in my mind at that time, I wondered what I did to encourage his affections, and I had to admit to myself, I was quite a flirt with all the boys I knew. It came naturally, and I never knew when to turn it off or dial it down. I had led this guy on without even knowing I was doing that, and often I was vaguely aware that boys had crushes on me due to my flirtations, and I stupidly encouraged them without any intention of making good on that. (I think they used to call that personality a “tease,” but it was not intentional.) I meant no harm and I was just young and naive and I did not understand a thing about possible reactions to my friendliness and flirting

I felt remorseful and guilty about Paul after being so rude to him but did not try to repair the situation at the time. I had no idea how to repair it. As a follow-up, because I know you want to know what happened next, he just avoided me from then on. There was little to no interaction or opportunity to apologize or have a talk with him.

For someone not that attractive or fully developed, I sure was particular. Why are kids at that age so rejecting, cruel, and selfish? I am ashamed to admit that I was all of the above at that moment in time. I was no better or more attractive than this guy, and here I was thinking to myself at the time, “AS IF!”

In fact, this is one of those memories where I wish I could push a rewind button and handle it differently in a more mature way.

He was a nice guy, not a bad looking boy, and he sure went to a lot of trouble to give me a sweet Valentine’s Day surprise. If I could, I would go back in time. I would graciously accept his gifts with a smile, and give him a little peck on the cheek. In my gracious gratitude, I would act like he was the most heroic, handsome guy on the planet through his surprise presentation for me, in order to gift him back with the moment he so obviously wanted on Valentine’s Day in 1969.

So tall, blonde-haired, bespectacled, slightly pimply Paul, who was a Chad of “Chad and Jeremy” lookalike, if you are out there somewhere, I am remorseful and ashamed of my selfish fourteen-year-old former person. It is my fervent wish that things got a lot better for you on each of the subsequent Valentine’s Days that followed.

Would love for you to share your own Valentine memories in comments below.


  • It didn’t happen on Valentine’s Day, but a boy I had gone out with to a semi-formal came to my door with a pretty drop necklace. “Now, will you go out with me?” He asked while I gazed at the shiny piece of jewelry. “No,” and I closed the door. Still, to this day I don’t know why I did that, kept the necklace and all.

  • My first Valentines gift from a serious boyfriend was big stuffed animal with a radio in its rear end!

  • Your blog post brought back so many memories of having the wrong valentine. I was pretty forthright about it, and tried to be friends with those fellows. I’m sure it would have been kinder just to slam the door.

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