Here’s Derek on some structural problems with dating in this modern world:

There ought to be a class for people who positively suck at talking to members of the opposite sex.

This thought occurred to me the other day. I mean, let’s presume for the moment that you were not the sort of person to pick up that social skill-set during high-school. Where exactly are you going to learn it in today’s society?

First impressions, especially on the topic of romance, are so terribly crucial, and if you screw it up, it doesn’t matter how much chemistry you and the other person might have had if given the chance, it’ll all be for naught because the first impression will have already been blown.

Meanwhile, you really have no constructive feedback loop on what it was that made it “not work” for them in the first place. Sure, you can try and approach the problem “scientifically”, trying slightly variant versions with different people and seeing which ones garner the best/worst responses, but that’s not exactly the point of the entire operation, and certainly isn’t an efficient use of a scarce resource (that being “available members of the opposite sex”)
…
Here’s the worst part, in my opinion — It causes you to doubt the value of the attempt itself. You start saying things to yourself like, “Why bother, it’ll just be another annoying exercise in wondering what little thing I did wrong this time?”

Admit it, everyone out there has had times in their life when they thought that, a time when they would say to themselves, “Why should I bother putting it all on the line to get rejected, knowing that I’ll probably never even know why I was rejected?”