When It Comes to Dating, Should You Play "Not to Lose"?

Back in high school, our coaches constantly warned our soccer team against "playing not to lose." I never understood what that phrase meant until recently, when I applied it to dating.

Back in high school, our coaches constantly warned our soccer team against "playing not to lose." I never understood what that phrase meant until recently: Indeed, our soccer team was often guilty of doing just enough to win, but not doing enough to ensure that victory would not be snatched from us somehow.

Once we were up by a goal, we'd just coast from there, control the game, trying not to concede the tying goal — but never pushing for that second goal that would have ensured victory.

This "playing not to lose" mentality has dogged me my whole life. I do just enough to get by, but not enough to ensure success.

In dating, I have the following mantra:

"I'd rather save face than risk looking bad."

Sure, things might work out and I could date the girl of my dreams. But if it doesn't work out, and I try too hard, I might end up with egg all over my face. In the end, I'm happier ending in good standing while coming up empty rather than giving 110%, failing, and leaving everyone with a bad taste in their mouth.

Here are the ways I can look bad if I "play to win":

Looking Like a Stalker

I have strict policies: Do not follow up on calls. I mean, if a girl wants to call me back, won't she call me after the first call? And if she's trying to get me to chase her a bit, I've already done so after one call, in my opinion.

This explains why I'm nervous to so much as post a "hello" on the Facebook wall of the girl in question if I haven't heard back from her in response to previous correspondence. The only way I'll contact someone again is after a month or so — at least then she might not remember that she didn't answer my last correspondence.

Looking Desperate

There is a risk to pushing for a date with a girl because, if it's done a certain way, it might make me look desperate. Besides, why should I try so hard anyway — it looks attractive if I'm "busy" with other things in my life, right?

At some point, a woman will think: "Doesn't he have anything else going on in his life other than trying to get me to go out with him?"

Looking Clueless

Of course, if I don't show my crappy game too much, there won't be much for her to criticize. The fewer moves I make, the less possibility there is for me to say something stupid, say the wrong thing, or say the right thing the wrong way. And we all know I'm guilty of this quite often.

So where does that leave me? It puts me in a tough place, considering this Mark Twain quote that my sister sent me the other day:

"Twenty years from now you will be more disappointed by the things that you didn't do than by the ones you did. So throw off the bowlines. Sail away from the safe harbor. Catch the trade winds in your sails. Explore. Dream. Discover."

I agree, in theory. But all too often, the "safe harbor" is tough to leave, especially when I would rather maintain good standing in a woman's eyes than risk looking bad.

Hopefully, the problem is not so much inside me, but more of a function that I have not met anyone worth "looking bad" for. There's definitely a confidence issue at play here. Lack of confidence leads to less risk-taking.

Have guys ever "lost good standing" in your eyes by persistently hitting on you? Do you agree that sometimes it's easier to not risk looking bad? Or is it impossible to look bad if a woman is really in to me, no matter how bumbling I am during a courtship?

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