I think you are over thinking it. It's great to meet new people, and when you have the opportunity, and he's not a freak, then I encourage you to take it!
Some people try to protect their own low self esteem by listing all of their faults up front. Then, when it scares the other person away, they feel that it was inevitable because of what ever problems they have. But that is a sure recipe to drive people away.
Instead, be interested in others, and don't focus on yourself. Be fun and engaging and see if you enjoy their company. The other person has the right to decide if they are interested in a friendship or not, as are you. If they are not, it can be for a number of reasons that you might not have even considered: your value systems might not be in sync, you have differing interests, your personalities are not compatible, etc, etc. It might have nothing to do with your own perception of your own inadequacies.
On the other hand, you might be very compatible, but if you are laying out all of your own insecurities up front, then you might never find out if you have a chance at friendship. That would be really sad.
Honestly, the most important thing in any beginning relationship is to take interest in the other person. No one wants to be around a self centered person, even when that person is self centered in a self-deprecating way. If you are interested in his thoughts, values and interests, he will more likely be interested in yours. But if you start off the conversation with a list of disclaimers, it's not very likely that you'll get much past the first conversation.
Enjoy your conversations. If it leads to a friendship, great! If not, that's good too because it wasn't meant to be. Relax and have a good time.
