"risk aversion jets set a little high.."

Good one!

I'm adding it to my list of terms I like, which includes "pulling up your big-boy pants", which is what this poor soul needs to do.

LW: I'm realizing that I'm an irretrievable mental defective.

Drama queen is right. And this statement prompts a question: If he's so "irretrievable," then why write to an advice columnist in the first place?

I'd have written him back with something like, "You're right. You're doomed to a life of missed opportunities, and you'll die lonely and impoverished because of missed opportunities. Sucks to be you."

When I read the first sentence of this letter, I have to admit that I was expecting our gracious hostess to lay into this guy and do everything short of calling him a pussy. I was very happy to see that the response was none of that.

LW: You're not a mental defective at all. Every man in the world has these same moments. Amy will often talk about her boyfriend in her responses to similar letters. How he grew a pair and manned up and approached her in spite of his natural aversion to such exchanges. What she may not realize is that he probably has had hundreds of such opportunities that he didn't act because of a similar train of thought.

Brace yourself for all the comments that say things like, "pull up your big boy pants", etc. The fact remains is that every man, who is single, goes through this sort of thing about once or twice a week. You're probably just not used to being single. There is nothing abnormal or defective about it. It's fucking hard to approach women. Even if they are actively flirting with you, it's hard to spot until you get some distance from the situation. Of course, by then it's too late.

You're not alone. This is just a part of being a man. At least we don't menstruate. So there's that.

Yeah, WDick, we're pretty impossible. Which is why you gotta pull up those aforementioned pants and get in the goddamned game.

No matter how the rules of dating change from decade to decade, the basics remain the same. No matter how hard it is to approach women,you'll never know how you'll do if you don't at least make an effort!

Which also goes for the other point he made: "The same thing happens with business opportunities. At the critical moment I need to act, I go into a fog of some kind, weighing my options."

"The same thing happens with business opportunities. At the critical moment I need to act, I go into a fog of some kind, weighing my options."

He needs those aforementioned pants for more than one reason, whistleDick.

But I suppose I can go for the kinder, gentler lines: Time and tide wait for no man. He who hesitates is lost. There is no try! There is only do or do not!

Better?

Well, shee-it. I looked a moment ago and my comment wasn't here, so I re-wrote it. And now, here they both are. I hate when that happens.

Patrick said >

Which explains why you don't make your living as an advice columnist. They tend to try to be helpful.

Laurie, maybe my response would have been helpful. Maybe it would have given him the resolve to solve his problems in an effort to prove me wrong.

Have you never in your life given the doomsday response to someone in hopes that it will wake them up?

So what do you do if you already are a bitter old man? (Other than trying to milk a telephone pole or drive a pirate to work)

So what us the storybehind the name whistledick? Because all these years i have been getting a very specific mental image nit unlike a tea kettle spout

To me, this reminds of all those times we think of something really great we could have said hours after an argument. One reason this happens I think is because of time to process. But another is that our brains are different beasts when in the middle of a confrontation vs processing it while sipping a latte in a comfortable chair. Diffeent chemicals running in there. And if this guy could realize that, he wouldn't beat the crap out of himself for ckoking.
That and give up the expectation that these things are supposed to be easy. Learn how to oprate in tense situations. And like Amy said, learn that rejection is painful but not deadly. But what might make it unbearable is that self beating he might give himself if he wasn't succesful.

Women face this same issue, but they hide behind convenient "social roles" that discourage them from EVER taking action. Why didn't Cute Girl approach HIM? Oceans of opportunity pass by them this way!
I still wonder where my life would be, if I hadn't acted the same as LW, when that beautiful blonde coed was coming on to me at the nude beach. It was a long time ago--THOSE opportunities don't happen every day!

There it is. There's the "pussy" insult.

As Dave pointed out, this is something that everybody goes through -- women also. It's very common to kick yourself for not acting in the ideal manner in some situation. Much like the great comeback during an argument that you think of too late.

It doesn't make you a pussy. Sometimes you get it right. Most of the time you don't.

This letter writer may, in fact, be socially paralyzed to some extreme degree. I'd bet that isn't the case. He's probably just like all the rest of us.

One thing that he might try to keep in mind is that a swing and a miss when it comes to asking a woman out actually feels pretty darned good when compared to the frustration of inaction. However, this is way more easily said than done.

If the LW is going to keep passing up opportunities anyway, he could improve his mental state by developing a sour grapes attitude toward them. Concentrate on how that pretty girl might have married and divorce-raped him, or how that business opportunity could have been a scam.

Sometimes it will even be true. In my own life, there are very few chances I regret passing up; rather more that I wish I had.

I also wonder if it is playing back in his head and possibly changing the situation.

At the moment did it seem more like it was a just a friendly smile -- not an open to be approached smile. as it was played back maybe it became more flirtatious.

I made a major career decision many years ago and I would later beat myself up over it because it turned out to be a poor decision -- or more like a different one would have been a lot better. When I was going through my career counselling from being let go from the bank the person made a great point -- I was evaluating the decision with a lot more knowledge than was available when the decision had to be made.

Remember the sayings - strike when the iron is hot and only fools rush in.

With women and business success, you need to get to the point where you don't care—or at least fake it.

There was a Japanese classic going around business schools a few years ago. IIRC, it was called 'five rings'. It was about how to be a successful samurai. You had to not care if you lived or died. Only then could you use your skill and training to the greatest effect. It was supposed to inspire MBAs to take risks.

Book of Five Rings 五輪書 (Miyamoto Musashi)