Real stories about dating and relationships in New York City. Truth is more interesting than fiction.

Winning and Losing

Winning and Losing i am not a role model  841885 84438052 196x300Here’s a random thought for you – when it comes to dating and (or life), it’s probably not a good idea to think about winning and losing.  Winners or losers.

Nope, not a good idea.

Here’s a story - I have a friend, a married friend.  She was unhappy.  I’d say unhappily married, but that wouldn’t be entirely accurate.  She was unhappy in her life and that made it impossible for her to be happy with anything, her marriage included. Anyway, she got herself involved in a very messy affair.  I say, “very messy” because they were both married and both couples knew each other/were part of the same professional community.

From the very beginning she kept telling me that she did not love this other man. That she was just unhappy (I’ll leave the other details out). But then, after many months, things shifted.

At first, it was the other man who was doing the pursuing. And he’d said a lot of things. Said he loved her more than his wife. Stuff like that.

And she really like hearing stuff like that. So much so that after a while, she decided that she wanted to hear it more often. All of the time (yeah, I’m simplifying). So she asked him to leave his wife. For her. And then he flipped out and said he couldn’t. Wouldn’t.

At which point my friend started to want him more. She became determined to get him to leave his wife. For her. Which seemed insane to me, because just a few months earlier she’d told me she didn’t really care about the guy, at all.

Her reasoning (because I did ask), was that she couldn’t stand losing.  She was actually motivated by the fact that he picked someone over her. Her competitiveness kicked in, driving her to compete for him. Aggressively.

All the while, her husband was willing to give things another try. Go to counseling. Whatever. But she was focused on winning.

So that’s their story. Or, at least, part of it.

I’m also freakishly competitive, in my own way. And so I get it (not the cheating on your husband with a married man part, but the not being able to accept being second best part). And I’m also willing to admit that some of my own dating and relationships behavior has been motivated by this whole winning/losing mentality.

I’m going to cut us some slack here.  We’re raised to be hyper-competitive. To see everything as a challenge. To strive to succeed and overcome every new obstacle. So it makes sense in a sick, twisted and completely wrong kinda way that when a person doesn’t love us back, we see that as losing.  But only in a sick, twisted and completely wrong kinda way…


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8 to “Winning and Losing”


  1. Terry says:

    Sadly I was drawn into the need to win. Car dealers do it all the time- so do home sellers — “someone else is bidding on this car…house…lady…” Years ago- I started dating someone and I was one of four — I won, and then threw the prize away.

    They say that some cheat because they are not getting the attention from their significant other – or affirmation – or something. So they find it “easily” from another — then the competition begins.

    Real competition isn’t to get the love of another person – to get the affirmation from them. Real competition is the marathon – not the sprint. To stay in the race.

    • Simone Grant says:

      I don’t think there are too many people who haven’t been drawn into ‘the competition’. Maybe people who marry their high school sweethearts and stay blissfully in love, together, for their whole lives. But they’re pretty rare.

      I’d agree with you, the real competition is the marathon. And each of is really competing, kinda, against ourselves. Our worse demons. Maybe.

  2. I recently was faced with my own win/lose mentality in a slightly different context: jealousy. My boyfriend is in close contact with his ex-wife because they have joint custody of their daughter. I know their relationship is WAY over and my boyfriend has zero interest in being with this woman but their friendship was driving me a bit nuts because it’s pretty obvious to me that the ex doesn’t like me (I don’t think she really wants my guy back but she was enjoying having him as an emotional crutch and I’m now interfering with that). I was proud of myself for not letting my boyfriend see too much of that but it was making me personally miserable until a friend pointed out to me that my view seemed to be that whenever he spent time with her, it meant she was ‘winning’ and I was ‘losing’. But of course, that was entirely in my head. And even if I did insist on seeing it that way, the reality was that I had already ‘won’ – if ever actually forced to make a choice (which the ex has sadly done on a couple of occasions), my boyfriend chooses me (and if he didn’t, I’d walk). So the only person that the win/lose mentality was hurting was me. So the ex still bugs me but when I stopped feeling competitive with her, I became a much happier person…

  3. Matt says:

    For someone who makes his living on the idea that dating and romance is complicated (and thus something you can get better at with study and practice), I’m always bemused to see how simple much of it really is. People want what they can’t have. I’ve always likened it to a little kid who wants the ball when another kid has it and then loses interest as soon as he actually gets it, but I like the way you couch it in terms of people perceiving it as winning or losing better. (Although either way you slice the bread, it still ends up being pretty childish :D ).

    • Simone Grant says:

      I like to think of it not as childish (though it is) but rather giving in to our worse instincts. Because, let’s face it, we all have these feelings.

  4. Michelle says:

    Maybe this will be of some comfort, I read on another blog (or maybe it was this one?) that in the area of dating and relationships, you only need to win once. Dating is not a batting average. You can strike out as many times as you like, but once you hit that home run, it wipes out all the other losses. Hope this is helpful. :)