Skip to main content
Report this ad

Does playing it cool work with men?

Dear Diva,
I met this terrific guy and I didn’t want to blow it this time. I read all the advice and books about playing it cool and letting him come after you because men like a challenge… I did everything right, never showed my hand, and it worked- at first. One day when I thought things were on the right track, he tells me he doesn’t think it will work out because I obviously don’t take him seriously. He met someone that was much more open and wanted to pursue that. WTF??? I mean I was never mean to him or anything. Is it too late? Can I fix this?

Signed Blew-it in Bedford

Dear Shake-it-off,

Not only do I know this story, but I own the T-shirt. Actually, reading your letter gave me bad flashbacks. In fact the exact words “I never thought you took me seriously” were the same ones I heard. Yes girl, I too thought I was playing it cool. Not showing him too much of me, wouldn’t have a drink in front of the guy, made sure he knew I was not invested in him, made sure he knew other guys were pursuing me. Not ever calling or texting first, ignoring him when I saw him online unless he talked to me…Every date was an act, a game. Guess who won? He did. He finally decided that was not “what good looked like to him”, and found someone to love him the way he deserved. I got hurt.

The good news? I needed that slap in the face to change my dumb ideas about the way one treats a man and expects him to respond. I still don’t call first. I still don’t ask guys out- that won’t change. I don’t chase men, or throw myself at them. I believe if a man is interested, and you are what good looks like to him- he will show you. However, when I am fortunate enough to stumble on one who does show me he cares, I do respond to that. I do show myself to him- let my hair down a bit. I don’t “strategize” anymore for my dates. I go out with the guy, and try to get to know him, let him get to know me, and have fun. If he seems interested and I am as well- I don’t “act” like I don’t give a damn if he comes or goes then get all pissed and bitter about it when he goes. For me, the result of that was a very great real relationship over the past year.

Is it too late for you? I don’t know. I don’t know how long this went on for or how into this new girl he is. Have you talked to him? Apologized to him? Told him that you really do care and take him seriously? If you haven’t, I would at least suggest that. It may not work but it is redeeming for you to own your mistake and settle it for you. Warning: If the conversation turns to you becoming pathetic, clingy, needy, or beggy- you’re all done. You will immediately invoke the “Eew feeling” in him. Come on now we all know what that means because we have all felt it when someone liked us, that we didn’t and they crossed over the pathetic line. We also know how it feels when we have done so. At that point, its time to shake it off, cut your loses, learn your lesson and move on. Write me back and let me know how it turns out for you.

Love, Diva

Have a dating question? Email me:


Report this ad