What does it feel like to be unattractive and desired by none?
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I saw one element that struck home with me:
I also get to hear female friends go on about what jerks all men are, how they cheat, aren't trustworthy, etc
It stood because I learned the hard way that when you are that guy you're the brother she never had or (put in the "Friend Zone" [hat top to the movie "Just Friends"]). The problem is that excessive assertiveness by people of limited height tends to come off as "Napoleon Syndrome" (HNers know Napoleon wasn't actually short, but I'm guessing my point was made properly (-:).
HN tends toward problem solving, and I had the confidence problem, myself. I am not short, but I am probably in the bottom 25% of the "attractive scale". I'm a very skinny, non-muscularly developed male. I have an egg shaped head and various other features that my bride (of 7 years, who happens to be a three inches short of 5', likes to joke about). I was terrified of rejection from women because I had been rejected a few times previously and ... really, it sucks.
I can't take credit for all of this because I had read something "way back when" that led me to this plan. I did it. It worked for me.
First, I wrote out the plan. This was important because it reinforced that I was solving a problem in a non-personal nature (think serial killer saying "It puts the lotion on its skin or else it gets the hose again"). At least once per day (ultimately turned into several times in a two day span), I would subject myself to female rejection in every way, and I would accept it graciously.
I had been juggling one "friend I had hoped would be my girlfriend" and it wasn't working out, so I started there. I explained that I had feelings for her in clear language (I believe the words were "I've been hanging around with you as a friend in hopes that you would date me"). I apologized for not making that clear in the first place (the whole graciously part kicks in. This was, in my mind, a lie). I got rejected. We also ceased to be friends. In the long run, it was a good decision.
Baby steps: I went to the bar (really, a club). I used to triumphantly say that I'd never want to have met my wife in a bar. This was a cop-out, and I found clubbing to be a great sandbox environment for this reason (I don't "want" to meet my wife in a bar, so if they reject me, it's all a big experiment). I don't dance, not even now. I went there with one of my friends (significantly more attractive, despite being as skinny). He actually took home one of the girls who had rejected me (really badly, with the whole "how dare you hit on me at a bar on ladies night when I got half-off drinks and no cover charge and you had to pay for the privilege of me berating you [yes, still a little bitter about that]). I struck out -- continuously -- mercilessly -- and the first several times it was seriously one of the biggest ego-killers I'd experienced (though, the amount of concentration it took to keep a cool head actually softened the blow for me).
There were, however, the few wins. I got a couple of good dates out of women I met at the club (no real connections). I was (naively) surprised to find that there are women at clubs who are there because they can't find another socially acceptable place to be "picked up" (look for the ones who aren't drinking very much and lack the ring or the arm-attached boyfriend).
The practical upshot of all of this was the usual story of how to gain a life skill (confidence, not womanizing). It was highly awkward, painful and resulted in a lot of failure. But I'm happily married going on 8 years as a result of it. And the experience increased confidence in communicating with others across the board.
EDIT: phrasing wasn't ideal.
I mean, with the latter he's not giving much away, and he might at least be able to attract attention from people who were looking for someone nice to be with who isn't shallow and self absorbed.
Also, if you're in this sort of a situation, I find that taking part in organizations where beauty isn't a primary value (religious and charitable institutions, political and social causes, for example) would let you get to know people better than just going in the deep end of the shallow, sex focused "dating scene" .
I believe the answer lies in his statements about lacking confidence.
I completely agree with you regarding meeting someone in social situations where something other than "dating" is the primary purpose. From personal experience, though, those circumstances are more difficult to approach a person you're attracted to (unless they are specifically geared toward meeting people (for relationship purposes) within a specific shared interest). Nonetheless, if you lack confidence to approach a prospective mate, the setting won't matter much, you simply won't approach someone you're interested in.
Personally (as I had written previously), I advocate diving in head first into the "dating scene" without prejudging the scene. You've referred to it as shallow and sex focused. It doesn't have to be. Commit to not having sex until you're married, or some other meaningful milestone and approach the dating scene that way. I didn't find my bride in the shallow, sex focused dating scene, but I would have never approached her if I didn't have the practice that said dating scene gave me. I believe, in most cases, men have a one-up that the person answering this question failed to take into account. Most men place a far higher value on physical attributes than women do (though, height is one of those attributes that seems to be very important to the women I've known, so I sympathize with this gentleman ... being skinny and not muscularly developed tends to follow pretty closely, though ... and I'm in that camp).
I remember how difficult it was at the time, and how insecure I was, but it got easier and I wouldn't have met my bride if not for the miserable experience of submitting myself to rather consistent rejection.
"This is a follow-up to: What does it feel like to be attractive and desired by many, Stack Overflow?"