I think the reason people have trouble dating isn't because of their skills or who they are. That should be a relief for most people wondering if they'll ever learn to date well and have the intimacy they wish for deep down. Instead, I think people have trouble because anxiety makes them flip out and think they have to get rid of the anxiety to be themselves. The "flipping out" causes them to detach from who they are in that moment and when that happens, they forget why they're valuable. That's when people get sad and hurt and then turn the hurt into something else like blame or irritability or avoidance. But the key is that they forget why they're valuable and why they're entitled to relax, make mistakes, and still retain their value. It's all about value.
The typical person goes on a date and feels anxious. They think their anxiety says something awful about them or is going to cause something awful to happen (like rejection) so they start thinking how they can change who they are. They reject themselves, often taking on a more comfortable--but ultimately fake--role. They focus on what they lack instead of what they possess, and forget all the things that makes them pretty fucking great. By the time they're on their date, they think they need to hide who they are by pretending to be someone more capable, more interesting, more confident, more assured, even though they naturally possess those qualities (usually) to begin with. Deep down, they don't feel like they deserve the person. They feel smaller and lower, submissive. If you really study relationships, you'll see that lots of times the other person feels the same way. Isn't it ironic, don'tcha think?
When they find a way to remind themselves of their value, perhaps by talking to a friend or by reconnecting with their feelings or reviewing why they're not awful losers, they start to feel hole again and forgive themselves for any shortcomings they may have or errors they might make. They have a sense of natural hope that isn't forced. It's what you'd call security, as opposed to insecurity. Good therapists, good friends, good techniques help you cultivate that.
Question? Write me. Anything. As long as it's not stupid. (I'm not really sure why I do this anymore. ;)