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Dating Advice For Young Gentlemen, Part I: Meeting Somebody

Updated on May 24, 2014
How Do You Do, by  Isaac Henry Caliga (1857-1934)
How Do You Do, by Isaac Henry Caliga (1857-1934) | Source

We all flounder a bit when we’re starting out in life—there’s no way to completely avoid this. I was the oldest kid, and I had to figure out a lot of things on my own, socially. My parents, well, they did their best, of course, but I never really felt comfortable talking with them about dating, and I doubt they felt comfortable talking about it with me. I had to make do with lessons gleaned from books, movies, and syndicated TV shows. Needless to say, this made for a few disasters in my early social life.

My eldest son is eleven years old now, and about to embark on the turbulent tween and teen years. Sooner or later, he’ll be thinking about dating. He hasn’t asked me for any of this advice yet, and probably won’t for a while. He may never ask. But here’s some of the stuff I’ve managed to figure out in retrospect. None of this advice will turn his (or anyone’s) teen years into smooth sailing, but there’s a chance it might help him and others navigate the storm without running aground or taking on too much water. Maybe there are some parents out there who aren't sure how to talk to their sons about dating, and these words might help them out, too.

A caveat: This is not a series about “how to get dates.” There are plenty of those around, and almost none of them are any good if you want to have a meaningful, mutually fulfilling relationship. Also, I was never very good at “getting dates” anyway. What you’ll find here is advice on how to conduct yourself when you’re interested in a girl so as not to seem scary, how to deal with her reaction to your interest (whether she says no or yes), how to act (and how not to act) when you’re dating, and how to deal with the (highly probable) end of your relationship without acting like a complete prat.

Finally, sorry ladies, this advice is written with guys in mind. I’d like to imagine that most of this advice applies to girls as well, but I’m probably wrong. You’ll have to tell me: I know nothing about what it’s like to be a teenage girl. I can only guess. One of my guesses is that….

If You Think She Doesn’t Know You Exist, You’re Probably Both Wrong And Right

If you go to the same school, and the school’s student population is less than about a thousand, chances are that the person you like is at least aware of your existence. She would probably at least say, “Yeah, I think he goes to my school,” if someone asks her about you. But unless you talk regularly (you’re in some classes together, you’re in some of the same extra-curricular activities or clubs, you go to the same church—that is to say, unless you actually know each other) chances are she doesn’t think about you all that much. That’s okay. When was the last time you thought about the girl who sits two rows over from you in history class?

Okay, sure, if the person you like happens to sit there, probably ten minutes ago. Pick a different desk: when was the last time you thought about that girl? If you and she are also both on the debate team, you probably thought about her in the last couple days. If all you have in common is the same history class, you might not have thought about her all week (except for when you were in the same room together). The point is, unless you have (or want to have) some connection, you’re probably not thinking about a person you barely know unless she’s standing in front of you. You need to understand that the same rule applies to the girl you’re crushing on—she probably is aware that you exist, but (unless, as mentioned, you actually know each other) she probably doesn’t think about you all that much. Luckily, it’s really easy to fix this.

All you have to do is walk up to her and say hello. But it’s important to remember that….

Parents: Respect Your Sons' Feelings

It's very easy, as adults with the turmoil of adolescence behind us, to be dismissive of our kids' crushes. This is a mistake. We may think we know better--that a little perspective will sort the kid out--and this is probably true, but that doesn't help your kid deal with his emotions even a little bit.

Youth cannot know how age thinks and feels. But old men are guilty if they forget what it was to be young. --Albus Dumbledore

Think back to when you were fifteen and got turned down or dumped for the first time. I don't mean to look back with the benefits of age and experience--that won't do your son any good. I want you to remember how you felt at the time. Remember the crushing dispair, the utter wretchedness, the rejection. Perhaps you felt like nobody would ever love you again. Perhaps you worried that everyone at school would know about how you made a fool of yourself, and would make fun of you for it. Remember how intensely you felt these things and how important they seemed at the time.

You have the benefit of probably thirty-five years of experience or more. Your son does not. What's more, your son is dealing with a very volatile mix of hormones and insecurity. He's interested in dating for the first time, but just when he wants to look his best, biology is making him break out in pimples and grow out of his clothes before they even fit properly. He wants to be treated with more respect, but isn't quite sure he deserves it yet. He's stuck at school every day with a few hundred young people just as confused and volatile as he is.

You've been through all this, and can remember how it feels, if you try.

Keep this in mind when you see your son dealing with this emotional maelstrom, and never, ever make light of it. If your son feels worse about himself after talking to you, he'll learn to stop talking to you at all.

If She Doesn’t Know You, Then You Don’t Know Her

This may come as a shock to you, but it’s true. You may think you know her, but you can’t get to know anybody without talking to her—and listening to what she says—for quite a long time. You only know what little you’ve seen her do, heard her say, and perhaps heard people say about her (which is not reliable information). You also may have a guess based on what kind of music she listens to, which classes she takes, which activities she’s joined, the style of clothes she wears, what have you. But you’re probably wrong.

This is probably the most important thing for you to figure out when you’re a teenager: no matter what you might think about someone, if you’ve never really talked to them, you really don’t know them. Since you don’t know much about this person other than what she looks like, we’ll assume that you’re crushing on someone you think is attractive. Your reasons for thinking this are unimportant—maybe you’re a bit of a nerd, and she looks bookish and intellectual to you. Maybe you’re an athlete, and she looks like she’s into fitness. Maybe you’re a neo-hippie and she wears peace-sign-earrings and torn jeans. Or maybe you’re attracted to a person who looks like she’s very different from you. Doesn’t matter. The point is this: physical attraction can be really powerful. It’s very easy to make the mistake of assuming that someone you think is good-looking is also going to be nice.

So now that you realize that while she might be pretty (whatever “pretty” means to you) she may or may not be nice, you’re ready to go talk to her. Keep in mind that you might discover that you don’t actually like her after all, and you might feel less nervous about what you’ll say.

After you’ve talked to her a few times and gotten to know her at least a little bit, you’ll have a better idea if she’s someone you want to spend a great deal of time with or not. Go ahead and invite her to hang out with you, but keep in mind....

If She’s Not Interested, There’s Really Nothing You Can Do About It

TV shows and movies are full of bad advice about matters of the heart. They’ll tell you that all you need to do is prove your love and you’ll win her over, and it’ll be forever. Or maybe they’ll tell you that the best way to get someone’s attention is with a grand gesture, ’cos she might never notice you otherwise. Once you make your dramatic declaration of perpetual affection, though, she will realize that you’re Meant to Be™. Of course, sometimes, this doesn’t work right away, and you’ll have to spend some time winning her heart—keep at it and don’t stray, because it’s important to be true to the one you love. But unfortunately, all of this is wrong.

Grand declarations of love do not make people love you back. They creep people out.

This is especially true if you haven’t spoken with your intended more than once or twice. (Pro Tip: “Can I borrow a pencil?” doesn’t count as a conversation.) If the object of your affection isn’t interested, learn to live with it. There’s nothing you can do to “prove your love,” and even if there was, there’s nothing—literally nothing—that you can do to get her to return your affections. Some folks will tell you that there’s a fine line between persistence and stalking. They’re wrong. The line is pretty clear. You can ask someone out once. If you get turned down flat, that’s it: don’t ask again; she’s not interested. If she says, “Sorry, I can’t this weekend,” or some other answer that leaves the door open for another time when she isn’t busy, then you get to ask one more time. That’s the limit.

If you don’t get a yes on the second go, you probably won’t get one ever. If you keep trying, you’re going to become an object of pity and/or ridicule at best. At worst, you’ll be a creepy stalker as well. Nobody wants to be that guy, and more importantly from your perspective, nobody wants to hang out with that guy. Usually when someone tells you that no means no, they’re talking about sex. But it’s also true that no means no when you’re just asking someone out. If you won’t take no for an answer when all you’re asking is, “Wanna go see a movie this weekend?” how can you blame a person for assuming that you won’t take no for an answer when you’re alone later?

No doubt you’re thinking, “You don’t understand! My intentions are honorable. I just want a chance to—”

Let me stop you right there.

You get lots of chances to show people who you are every day. It’s called being social. Talking to people. Learning who they are while they learn who you are. Sooner or later, you’ll catch someone’s interest without making a grand gesture or pestering her for weeks. Wouldn’t you rather be with someone who’s maybe a little bit interested in you already? Because let’s face it: pining for someone who isn’t interested in you may sound romantic, but it’s a waste of time. It’s also probably a waste of opportunity, because while you’re sitting around writing bad poetry about the girl who won’t go out with you, you’re probably not noticing that there’s another girl who would love to go out with you, and she’s kinda cute, herself. You might even have a thing or two in common, but you’ll never find out if you’re spending all your time obsessing and/or feeling sorry for yourself. It’s not an easy thing to hear—it’s even harder to put into practice, but the absolute best policy is….

This Kind of Thing Doesn't Work in Real Life

When You Get Turned Down, Suck It Up and Deal

This is not to dismiss the power or intensity of the emotions you’re feeling. When you’re fifteen, you love hard and fall harder. Getting turned down hurts badly; getting turned down by a girl it took you days to work up the nerve to talk to can be apocalyptically crushing. And it will happen to you. When it does, it’ll feel worse than anything I could possibly imagine if it hadn’t also happened to me when I was young. So yeah, I understand. It may have been a long time ago, but I remember it well. I also understand that this agony is intense, but temporary.

And it’s also very fair.

It's Heartbreak Hotel, not Hearbreak Permanent Residence

Heartbreak Hotel, by Ebyabe/southcentral
Heartbreak Hotel, by Ebyabe/southcentral | Source

No, Really! It’s Totally Fair!

Think about this, fellas: Imagine how you’d feel if someone you felt no attraction to asked you out. How would you respond? Would you feel obligated to go on that date? What if she told you that you aren’t giving her a chance, that if you got to know her, you’d see how wonderful she really is? Keep in mind that we’re not talking about some attractive stranger: you already sort of know this person and she’s not attractive to you in any way. Imagine the most obnoxious real girl you know (from school or wherever, but from real life). That’s who wants to go out with you. Right. Are you obligated to go out with her? No, you’re not, are you? Now, remember how you felt about being turned down by the girl you like? That’s how Ms. Wrong feels about being turned down by you.

If it’s okay for you to turn down people you don’t want to date (and it is!), it’s okay for people to turn you down, too. If you feel awful when girls turn you down, girls probably feel just as awful when you turn them down, too—and their feelings are just as real and just as intense and just as important as yours are.

This is not to say that you should go out with people you don’t like just to be nice (nobody will have fun on that date!), but rather that you should treat people as kindly as possible if you have to turn them down. Your words and actions can cut, even if you’re careful. And really, as we'll see, it’s kinder in the long run to be turned down (or turn someone down) flat rather than to go on a date (or a series of dates) where it’s clear that one person really doesn’t want to be there.

But I don’t want you to imagine that you’ll never find a girlfriend. In fact, if you’re like most guys, you’ll probably go on several dates and/or be someone’s boyfriend at some point between your freshman year and graduation. We’ll talk about how to conduct yourself as half of a couple next time.


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    • harrymelcars profile image


      4 years ago

      Lovely article - thanks for your insights.

    • profile image


      5 years ago

      Thanks for this great and informative article. A lot of parents find it very difficult to discuss relationship matters with their children, and this is a very big mistake. If the children don't learn it at home, they will learn it from outside, especially from their peers. And these peers may mislead them. So the best place for a child to learn about dating and relationship generally is the home.

      For more information about relationship, this blog: may be of help


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