Lately, there’s been a fun little “what if” floating around: Would you let your daughter date a young Donald Trump—back when he was in college? Kinda random, but it gets people thinking.
Back in the late ’60s, Trump was a student at the Wharton School at the University of Pennsylvania. Even then, he was known for being confident, ambitious, and, well, pretty sure of himself. He wasn’t the quiet, study-all-day type. He liked attention, wanted to be big, and made that clear early on.
There’s even an old story about him going on a date with actress Candice Bergen during college. She later said he was nice-looking but not exactly her type. The date didn’t go anywhere, and she was back home early that night. Nothing scandalous—just a quick dinner, no chemistry, and that was that.
So, here’s the question: if your daughter met someone like that—confident, flashy, maybe a little too into himself—how would you feel? Would you give him a chance? Or would you be worried he’s all about image and status?
Some parents might look at his ambition and say, “Hey, at least he has goals.” Others might see red flags if someone talks more than they listens. And let’s be real—teenagers can be pretty good at ignoring advice, especially if someone seems exciting or different.
But people do grow up. Someone who seems full of themselves at 20 might be a whole lot more grounded by 30. Or… not. It’s hard to tell when someone’s still young and figuring things out.
The bigger idea here is really about what we want for our kids. Do we want them dating the most confident person in the room? Or someone a little quieter, maybe more thoughtful? There’s no perfect answer. Every parent thinks about it differently.
Trump as a college student wasn’t that different from how he is now—bold, certain, always aiming higher. That’s appealing to some. For others, it might be too much.
So, if you were back in the ’70s and your daughter said, “I’m going out with this guy named Donald…,” would you say, “Sure, have fun!” or “Let’s talk first”?
Kinda makes you think, huh?