In every new relationship there are moments of truth. They are small moments. Many of us don’t even recognize them or even remember them after they’ve passed. But the way these moments unfold can make the difference between a happily ever after romance and one cut down before it even has a chance to begin.

That’s where leading comes in.

You can make goo-goo eyes at each other across the anime convention floor hall all you want. There still needs to be the moment where someone makes the decision to walk over and start a conversation. Leading can be non-verbal (taking someone by the hand, going for the kiss), or verbal, (asking for the phone number, revealing your sexual fantasy about the Kama Sutra Pirates).

I think of leading as anteing up. You‘re putting your money on the table (usually not literally), at which point the other person needs to either a) meet or beat your investment, or b) opt out of the game.

Leading isn’t about controlling the relationship. If anything, leading is about giving up control, because if the dancer(*) chooses not to follow, it’s the leader who ends up looking stupid.

Leading is about being willing to take risks. On a more practical level, it’s also about avoiding conversations like this.

BOY: Want to go out?
GIRL: Sure. What do you want to do?
BOY: I don’t know. What do you want to do?

And so on into infinity…

If you’re going to ask someone out, the onus is on you to provide direction for what you‘ll be doing. It doesn’t mean there’s no room for negotiation, but someone has to open the bidding.

Which brings us to the question, why does Boy get to lead? Girls can lead too.

They sure can. And if it works for you, go for it. Putting yourself out there when you don’t know how the other person feels takes guts, and I give mad respect to anyone--male, female, or other--that does it. Be advised however, in heterosexual dating circles, the woman leading goes against convention, so be prepared to face the following reactions.

1) Male insecurity. We’ve had it drilled into us from an early age that we are supposed to take charge. So when a woman does it for us, it can be a stab to the ego. Many women have run into this, and it’s what stops them from taking charge on a date. A friend of mine put it best: “It sucks when guys don’t have a plan cause not only do you have to take charge, you have to bring it up in a way that doesn’t hurt his feelings.”

You would think shyer or more inexperienced guys would welcome a woman who takes charge, but sometimes we take it the hardest because it reminds us of our shortcomings.

2) Suspicion. Often the more attractive a guy finds you, the harder time he’ll have trusting your motives. Instead of counting his lucky stars, he’ll be thinking. “There is no way THAT girl would ever have to ask a guy out, especially a guy like me. Either she’s messing with me or she‘s a murderous sex alien like in Species, and either way, I‘m not falling for it. And I‘m going to make sure everyone knows it by saying something mean to her.”

3) Inexperience. Most guys don’t get asked out a lot, which means they aren’t always going to know how to deal with it. I didn’t when it happened to me (**). We freeze-up and stammer and start looking around for the exits. It doesn’t mean we’re not interested. It means we don‘t deal well with unfamiliar social situations.

4) Dogs and cats living together, mass hysteria. When two people are simultaneously trying to be proactive, there’s going to be some clunkiness until they find a rhythm. The comforting thing about convention is everyone knows his or her role. On the other hand, those people bound by convention will never know what it feels like to live by their own rules.

The good news is, truly confident and self-assured guys have no problem with a woman showing a little initiative. The bad news is, most of those men live somewhere in the Andromeda galaxy. Here on planet Earth, truly confident men are a little thinner on the ground than one would hope. Kudos to you, if you’ve found one.

The last point about leading is that YOU DON‘T HAVE TO DO IT ALL THE TIME (***). Leading isn’t a way to prove what an mighty, in-control Alpha Male or Female you are. It’s a way of keeping a smooth flow while you get to know one another.

Good luck. The Kama Sutra Pirates await.

(*) I realize it would be less confusing to use ‘follower’ but I don’t like it. The word ‘follower’ implies blind obedience, which isn’t what we’re talking about at all. Plus ‘dancer’ sounds prettier.

(**) In my defense, the person hitting on me was another guy. Still, I felt dumb for not catching on sooner.

(***) Timing leads is a column on its own, but here are the basics. You lead a) during ambiguous/awkward moments b) as a response to a cue from your partner or c) when he/she has impressed you.