A chat with my younger self

Things I would tell the me in high school—once I get done Gibbs-slapping him

Hi there. If I’ve timed this right, you just started 11th grade and are about to do something extremely stupid. <slap upside the back of the head>

Never mind why you deserve that — you do. I’ll get to the particulars in a moment.

You spent the summer mooning over a girl named Wendy. You now have found yourself back in English class with her, just like 10th grade, which you weren’t expecting in a high school with over 4,000 kids, and you are getting ready to ask her out. Since this will be the first time you have ever asked a girl out on a date, you have prepared yourself for failure. You have prepared yourself for indeterminate results. You have not, when you think about it, prepared yourself for success.

It will turn out that success wasn’t anything you needed to worry about, so good allocation of planning resources.

You think you are prepared for failure, but you’ve only thought of the basic, simple, “Gee I like you but not in that way” sort of failure. You aren’t ready for soul-crushing, joy-extinguishing, life-is-gray-and-destitute failure, which is how you will interpret what is about to happen.

Basically because you’re a moron. <slap>

Sorry. In a few decades that will be known as a “Gibbs slap,” because—

Actually, never mind, that’s not what I’m here for. My point is, you will be crushed. You will obsess with what you did wrong. Your grades will suffer—not a lot, a letter lower in one or two courses, but it means you will graduate #11 in your class. Know what the top ten graduates get? A nice letter at the awards ceremony just before graduation. Know what #11 gets?

Good guess. Yep, you get nothing.

Anyway! Wandered off track. Sorry.

You like Wendy because…?

Ah, because Wendy likes you. Which you know because…?

She talks to you before class. And laughs or smiles at you in class when you say something funny. Yeah, bad news, kid—people like Wendy talk to anybody who listens, and even now you’re a pretty good listener. And she laughs because other people are laughing. Most of the time she doesn’t get your sense of humor.

Big red warning flag, by the way. Just letting you know now. If a woman doesn’t get your sense of humor, it’s not going to work. Not friendship, not romance. You and I have a strange sense of the absurd, an expressionless delivery, and a bad tendency to go for the cheap pun in conversations. It will make your date give you strange looks. Just letting you know.

Anyway, you will ask Wendy the Big Question. There will be a long pause—feels like a long time, in my memory, but it’s been a few decades—while she just looks at you with this blank expression.

Then she’ll start laughing.

You will not be expecting that.

You’ll pick up your books, walk over to another desk near the windows, and act like it never happened. You won’t acknowledge Wendy for the next two years, or act like you even see her. You will be terrified of asking another girl out for the rest of high school. When you get to college, you’ll ask out a female classmate by email, so that when she laughs at the idea of going out with you, you won’t have to see it.

Email? It’s like— tell you what, you slip her a note, how’s that? Cool.

The point of this conversation, oh younger dumber self, is to clue you in on something that took me years to figure out. Wendy, when she bursts out laughing, isn’t laughing at the idea of going out with you. I’m not sure she was even aware she was being asked out. She’ll be laughing because she thought you made a dead-pan joke of some sort. Because she didn’t get your sense of humor, and certainly won’t think of you as someone she would go out with.

Yes, I’m mixing up past and future tenses. So?

Okay, that does make this conversation two tense. See? Wendy wouldn’t get that.

While we’ve been chatting, I’ve been thinking. Sure, what you’re about to do was emotionally devastating. At the time. Okay, maybe for years after. But hey, you know who cares about high school class standing when you get to college? Precisely nobody. And the only thing worse than blowing the asking-out part would be going on the actual date, because you are so not ready for dating. You need a few more years spending time with real people, not the small group of geeks you hang with now, and learning how real empathy works and how not to be a total jerk who doesn’t understand people. You need to get some female friends—just friends, who think you’re weird but like you nevertheless—who will make sure you are properly prepared when you go on a real date. Which you will still screw up, royally, but your friends will have you dressed properly, at least.

Oh gawd, don’t get me started on how you dress. You look like you’re on your way to an “Are You A Nerd?” poster photo shoot. <slap>

Moving on. You are a hopeless romantic. Don’t give that up. You haven’t defined it to yourself yet, but you are on this quest to find The One. There are — speaking from experience — two approaches you can take when trying to find The One.

Number One: Adjust yourself to adapt to each woman you are attracted to. Learn what works, what doesn’t. Find what the object of your desire wants in a friend/lover/partner, and do whatever it takes to be that thing. If it doesn’t work out, try something else the next time with the next person, because doing what you tried before obviously didn’t work.

Option Number Two: Be yourself. The One will be the woman who is looking for the person that you are, not someone who is in constant suck-up mode. And remember that you have a list of traits for The One, as well. Don’t settle for less than the ones marked with a star.

Option Number Two is the best in the long run, trust me. But sometimes life gets lonely enough that Number One seems worthwhile.

Just saying.