I want her to ask me out!

Dear Lisa,

I’m a 32 year old male looking for solid relationship. I’m pretty good looking I think, and I don’t have a lot of trouble meeting women. In fact, I’ve dated a lot over the past couple of years. I’ve tried dating sites and being set up by well meaning friends, but nothing has really lasted longer than a couple of dates. I can’t seem to meet a woman who is really my type, and to be honest, it’s wearing me down a little!

The part I find the hardest, no matter how often I do it, is getting up the nerve to ask. It’s a little nerve wracking, putting myself out there every time. I’d love it if, for once, a woman approached me and did the hard work! What are my chances?

–Wishful Thinking (♂ Vancouver)


Dear Wishful Thinking,

I can appreciate how difficult and risky it is to approach a woman. However, I doubt that if it came down to it, you would actually want a woman to ask you on a date. My guess is that you would feel emasculated and resentful. My explanation is going to sound prehistoric, but for 99% of cases, it’s true.

For a man to ask a woman out (and I’m talking about a masculine man and a feminine woman) he goes through a bit of a process. He has to make the decision to pursue her, determine his tactic, get his gumption, and execute. It’s comparable to hunting.

Imagine you are a hunter. You spend spend hours preparing and practicing before you can feed himself – you have to get the gear, learn to use the gun, learn to track. You have to aim, and miss and then get up and do it again. Now, imagine if you did all of this preparation and as you set your sights on a dear, another somewhat less desirable dear leaps across the meadow, lands at your feet, lays down on her back and mouths the words “shoot me”. Feel emasculated yet?

What I’m trying to say here is that under your worn down veneer you relish the challenge of asking a woman on a date. I would even go as far as to say that it is in your nature! It is hard. It is terrifying to risk everything. It is a lot of work. But the glory of triumph is worth every second!

If your underlying question is: What are the chances that I will want to stay with a woman who asks me out? I’d say slim. Unless it is a one-time, twilight-zone, fate-acting-through-her sort of moment where she asks you out just as you were about to, and not a sign of things to come. More likely though, you’ll tire of being coddled after a while and leave her to find a woman who challenges you to be a man.

– Lisa



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