I find it interesting that this sounds like...my gen y brother. Why would he bother actually hitting on a woman, let alone pursuing a real relationship, when he can just stand around looking aloof and wait. His entire technique is the brake pedal.
The thing that is hard to imagine, for those who've never risked a real relationship, is that the terrible outcome isn't the remaining single. Being single is kind of great, if you can afford it.
The terrible thing is having never taken the heart-stopping adventure of a lifetime that a real relationship is. My brother may be good looking and intelligent with money and taste, but he has no idea that he's a wuss, a total prisoner of fear. He couldn't keep a self-respecting woman if he tried. He doesn't even know that he has to try. One day those empowered girls who don't know better than to throw themselves at bad-boy-wastes-of-time won't be remotely interesting to him, anymore. Maybe life will bless him with a cute meet that he doesn't let go of, that he's ready to become a man for, that he is willing to face his fears to keep. That's when he'll realize he wasted decades thinking fishing was about the hook when there's really a lot more involved when you've got a marlin on the line.
Don't make the mistake of thinking that relationship is about togetherness or commitment: the ability to make a relationship last is built on self-knowledge, on bravery and on being willing to evolve. The not liking what you see part of a relationship is the beginning of the good part. Falling for someone is the two hour line, the exhilaration and excitement. Don't let the look of the seatbelts send you running. Don't bail before the ride even starts. Yeah, it'll be scary and you might even feel awful later and lose your lunch. But at least you won't have missed out for being a coward.
I hope that wasn't too brutal. Thank you for having the bravery to share these thoughts in the first place. :)
This is a great post.