Dear Tony,

You're Making It Tougher

The dating game is hard enough. There are already enough rules, and you're just making it tougher on yourself by adding more rules of your own.

Duh! No wonder he's never had a girlfriend.

First off, I think one of the problems that underlies your inability to connect with a girl is your idea of when it is appropriate to initiate a conversation with a girl.

You believe in true love and romance? More power to you, and I hope you find it. But in order to see the fireworks, you must first light the fuse by talking to a girl you think you MIGHT be interested in.

100% Interested Is Utter Nonsense

I emphasize the phrase "might be interested," because if you've hardly exchanged a dozen words with someone, how can you know if you actually find that person interesting? The idea that you have to be 100% interested in a girl before you talk to her is, quite frankly, utter nonsense. Until you do talk to them and try to get to know them, the only thing you can be 100% interested in is your IDEA of what they're like.

Girls Make Good Friends

Furthermore, not every girl you talk to has to become your girlfriend; girls can make just as good – if not better – regular friends than guys.

How To Never Have a Relationship

The two main ways to ensure that you'll never find yourself in a relationship is to:

1. look too hard for romance, and
2. discount a possible relationship before it even has a chance to develop.

Don't forget the 3rd way to avoid relationships: be a control freak.

You're making both of these mistakes right now.

The Heisenberg Uncertainty Principle

As for the first mistake, I call it the Heisenberg Uncertainty Principle of Dating (break out your Chemistry 101 book if you need a refresher). The very act of searching for something alters the very thing you are looking for. You're interested in a girl, and want her to be interested in you, but in trying too hard to woo her, you begin to act unnaturally and awkwardly, which is generally a turn-off.

It's best to approach a situation with no expectations and just be yourself and take things as they come. Not every situation will be pure magic, and it's something you can't manufacture.

You're Afraid of Rejection

I agree. He should take one step at a time.

As for the second mistake: you're getting waaaaay ahead of yourself. It's always good to anticipate potential problems, but this is overkill. I would suspect, though, that your real fear isn't about time management, is about the possibility of being rejected.

Everyone fears rejection, so you're not alone. But please understand that rejection is all part of the game, even for the guys who seem to have all the luck with the ladies. Just like with fireworks, not every encounter with a woman will blossom into a magnificent and scintillating shower of affection; in fact, the vast majority of encounters will be duds.

But, you'll never know unless you initiate that spark, light the fuse, and see what happens. You're sure to get burned every now and then, but we all do, so don't take it too hard.

Relax

Relax. Stop thinking a possible future and focus on the probable present. Next time you see this girl, just talk to her. Relax, and just let the conversation go where it wants to... don't force anything. Relax, get to know her, and let her get to know you. And finally: relax!

– Shaggy