Play to Win

I was just playing a computer game, this combination zombie / Sim City style game called Rebuild, where you try to expand your city while at the same time keep your defenses up to guard against sporadic zombie attacks that you can't predict and don't know when will strike. I am pretty swamped with work at the moment, and don't allow myself much leisure time aside from socializing or seeing friends or spending time with girls... playing that game an hour or two a day is one of the few things I do to unwind these days.

Anyway, at one point in the game I was faced with a decision: I'd taken some heavy losses, and I had a chance to make a critical expansion, but to take that chance, I was going to have to leave myself vulnerable to attack. I might be attacked and lose the game if I took that chance, or I might not be attacked and I'd make a much-needed step forward. At first I thought, "No, it's too dangerous – maybe I should just play it safe and progress slowly." But then I realized, at the rate I was going, with the losses I'd already suffered, playing it safe probably wasn't going to pan out in the end. It was either play to win, and maybe win, or maybe lose on the spot, or play it safe, and probably die a slow death instead.

So, I took the chance – I played to win. And, as it turned out, I got attacked, and suffered a very heavy loss, and that cost me the game. I gambled and lost. But I was happy about it, because if I played safe I knew I probably would've lost anyway, just a lot more slowly. At least I took the chance. And when I thought about it, I could remember a few other times where I took similar chances and they paid off. If I always played safe, I probably would've lost all of those games.

Seduction, as it turns out, is a lot like this.

The Gamble

With every girl, there are these crucial junctures where you must take action: when you first move a woman or have her sit with you; when you first invite her home; when you first kiss her; when you first take her to bed. Those situations are smooth, effortless, and worry-free if you've been through them many times, and if you can tell the girl is going to be receptive. If you haven't, though, or you can't, those crucial junctures tend to feel like a gamble.

They feel like a gamble, of course, because you know that when you make that move, you will either succeed, or fail. Either she'll move with you – or she won't. She'll go home with you, or she won't. She'll kiss you, or she won't. She'll go to bed with you, or she won't.

The reason that most men on Planet Earth are not really all that good with women is because most men are risk-averse: they'd rather not try at all, then try and potentially fail. If they were playing that game I was playing, they'd rather play it safe and lose a slow death than play to win and maybe win big or maybe lose it all.

Something you'll notice when you meet men who are good with women is that many of the men who get good with women are really adventurous types; the kind of guys who very much enjoy taking risks. A much larger portion of the "talented with women" population is comprised of these kinds of risk-taking personalities than is the general population, I'd say. And it makes sense; if a man likes taking risks, he'll take more of them, and with women, that means he's going to have both more failures – and more successes. A penchant for risk-taking means a man's going to succeed a lot more in the long run with women than an ordinary man who shies away from such risks.

What Are You Playing For?

When I first started actively looking to improve with women and making myself push the limits of what I felt I could do, I'd routinely run into crucial junctures where I had to decide to play to win, or play it safe. And usually, because I'm a rather risk-averse cat by nature, I'd play it safe.

And then I'd lose the girl.

Some of the time girls were probably auto-rejecting and going cold on me because they felt like they made it clear to me they were interested, and since I didn't act, I must not want them. Some of the time they probably just lost interest in me for my not being man enough to give them what they wanted and step up and play ball.

Regardless, I soon began to realize that playing it safe wasn't really safe at all, and that, in fact, it was instead a more quiet kind of failure, where you didn't face the pain of rejection, but instead you failed by simply never giving yourself the chance to succeed.

There's a famous quote that I quite love by a past American president named Theodore Roosevelt, and it goes like this:

"It is not the critic who counts; not the man who points out how the strong man stumbles, or where the doer of deeds could have done them better. The credit belongs to the man who is actually in the arena, whose face is marred by dust and sweat and blood, who strives valiantly; who errs and comes short again and again; because there is not effort without error and shortcomings; but who does actually strive to do the deed; who knows the great enthusiasm, the great devotion, who spends himself in a worthy cause, who at the best knows in the end the triumph of high achievement and who at the worst, if he fails, at least he fails while daring greatly. So that his place shall never be with those cold and timid souls who know neither victory nor defeat."

What Teddy Roosevelt is saying is that the man who deserves our respect is the man who stands up to be counted and takes action and plays to win. And he calls those men who do not take action, who don't play to win, who play it safe and instead stand back and critique those men who are out there playing to win, the "cold and timid souls who know neither victory nor defeat."

Because, the man who plays it safe, that's what he gets: neither victory nor defeat. He gets nothing; he only just hovers there in limbo, dying the slow death of inertia as time marches by and other men fail and succeed around him while he stands still.

Play to Win

The day after I moved to California back in 2007, I had a first date with a really cute girl. We drove around under the palm trees, and she showed me the upscale part of town, and we stopped and had some ice cream and shared a few stories about ourselves. After a few hours, I took her back to my apartment, and we sat down on my couch.

There was a big gap of space between us on that couch, and I felt like she wasn't ready to be kissed. But I considered, and I thought back on those girls I'd lost by not trying to do anything, and I slid toward her and moved to kiss her. She dodged; then, she stood up, and said, "This feels pretty awkward; I'm going to go." I tried to get her to stay a little longer, but she would not, and she left. I tried, and I failed.

The very next weekend, I was out with another girl on another first date, and this girl told me again and again that there was no chance for us and we would only ever just be friends. Still, I led, and she followed; and when I had the chance, I started kissing her, and that night we became lovers.

Even today, 3½ years later, sometimes I still have to gamble and play to win. In fact, my girlfriend right now, when I brought her up to my apartment, she sat far from me on the couch, just like that girl from mid-2007, and I felt like she wasn't ready to be kissed, just like that girl from mid-2007. But, I slid toward her – albeit, a bit more smoothly than I did toward that other girl 3½ years ago – gently turned her chin toward me, and kissed her – and she kissed me back. She's quite a strong woman, and has a number of men pursuing her, and very quickly and unequivocally friend zones a lot of men; my guess is, had I played it safe, and not gone for the kiss when it didn't feel 100% on, and not slept with her on that first date, I never would have. But I wasn't playing it safe; I was playing to win, and that time, I did indeed win.

You really should always play to win. In seduction, in friendship, in business, in life. Know what you want and go after it. Because playing it safe not only saves you from failure – it saves you from success, as well. The man who plays to win wins a lot more often than the man who plays it safe. Even if you're like me and you're not much of a risk-taker by nature, do what you can to turn yourself into a risk-taker in practice. You'll see a lot more successes, and you'll win a lot more often. Then, you will never have to worry about being one of those cold and timid souls who knows neither victory or defeat, for victory and defeat will be the blood coursing through your veins that lets you know you're alive.

Chase Amante