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A simulation of a conversation I will perhaps be having in less than a decade: via ChatGPT.
A Grandfather, A Granddaughter, and the Lost Art of Teenage Romance
"Grandfather, since Bristol Grammar School was all boys when you attended, how did you even meet girls back then? Did you have to be very bold, or were there events where boys and girls could mix?"
A sharp question from my granddaughter, thirteen years old, newly curious about the past—not history in the dry textbook sense, but history as lived by someone she knows.
"We were very keen to meet girls," I tell her, "but there were none!"
I explain how, at fourteen, I attended a summer school fair with a group of friends, all of us determined to chat up some girls. "I knew immediately we’d have no luck as a group—packs of boys weren’t exactly irresistible. So I wandered off by myself, spotted a girl I thought was cute, and struck up a conversation. Rosalind—see, I remember her name!—must have thought I met at least her minimal requirements because we spent the afternoon walking together. My friends saw us, and they were so envious!"
"That sounds really sweet, Grandfather! And also very brave—you just walked up to her and started talking? I’d be so nervous! What did you say to start the conversation, and how did you know she was interested in talking to you too?"
"Sadly, it's all lost in the mists of time," I admit. "I had no experience at all in these matters—no films, no books or magazines on the subject, no internet or mobile phones. I think I was just a bit self-confident and under the illusion I had charm! Rosalind must have thought I was at least passable. But it didn’t last."
"Since you and your friends were all figuring things out without movies, books, or the internet to guide you, did you ever give each other advice about dating, or was it more of an every-man-for-himself situation?"
"We never talked seriously about it. I think boys didn't then—maybe they do today? Instead, we had a jokey ‘star system’ to boast about how far we’d gotten with a girlfriend. ‘One star’ was holding hands, ‘two stars’ was a kiss, and so on. It was all very innocent, and I never believed a word of it. We were all totally naïve and inexperienced."
"That’s really funny, Grandfather! I can imagine a group of boys trying to one-up each other, even if no one really knew what they were doing. Since you were all so inexperienced, did you ever have any really awkward or embarrassing moments when trying to impress a girl?"
"Always! We didn’t know the language of romantic interactions at all. We didn’t know how to behave at discos, how to talk to a girl-stranger. In the end, I think what worked was just to go with your instincts—don’t overthink it!—and be very attentive to the messages the girl was sending you, if any! You could usually tell, after dancing with a girl you’d just asked, whether there was any sparkle there. Then you’d offer to buy her a drink—probably a soft drink at that age!"
"That makes a lot of sense, Grandfather! It sounds like instincts and paying attention were more important than having a perfect plan. Was there ever a time when you completely misread a girl’s signals and ended up in an embarrassing situation?"
"Yes, but I have an acute sensitivity to embarrassment and would back off with apologies pretty rapidly. I was usually rather cautious in my interactions, and that tended to save me from stupidity. Not everyone was so circumspect, so don’t take me as typical!"
"Did you ever see one of your friends make a complete fool of himself while trying to impress a girl?"
"There are always buffoons around, complete show-offs. The girls laugh behind their hands and giggle with their friends. My friends were not people like that, thankfully!"
"Looking back now," my granddaughter asks, sensing we’re nearing the end, "do you think teenage romance in the 1960s was sweeter and more exciting because it was all so new and unstructured, or do you think young people today have it easier with all the ways they can meet and talk to each other?"
"Good question! If we'd been at a mixed school, my social life would have been completely different—I can't even imagine it. I read a lot about the terrible state of boy-girl relationships these days, but maybe most of the time I imagine it still works. A little empathy, consideration, and common sense go a long, long way. I wish you luck with the boys you meet, and I hope you choose well."
She smiles. "Thank you, Grandfather. That’s really good advice. And I think it’s really cool hearing about how things were for you—it makes me realize that even though times change, people don’t really change that much."
Maybe next time, she’ll ask about my first date. But for now, I’m happy she just asked at all.

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