Relationship-readiness uncertainty

I'm a bit old to be new to this thing (relationships), but I am anyway. Really I've never been in the [emotional] position to relate properly to another person on an intimate level. And while I'm by no means great, I know that I have a lot going for me (I really like myself as a person). Certainly I have close friends, and there is quite a whole level of relating here. But these are with guys; I'm talking 'with women' (I'm aware that woman are certainly - just like men – human, but relating is, at times, still awkward. There are mysterious underlying dynamics that do change things). I'm also aware that being able to develop a friendship is fundamental -– at least for me – in developing a healthy long-term relationship.

So the dilemma is: on the one hand I really long to be able to relate and build a healthy mutual relationship with someone, to give life to another person. On the other, I really need to develop a more thorough sense of self (to be able to sustain and maintain my own life), and also the fact that although I really like myself, there seems to be little correlation with a deeper 'likeability', in the eyes of other people (from experience).

So the question is: how do I balance developing friendships (which I may want to be more intimate) with the need to be develop a sense of self that is not dependent on others ?

I like your post. I see alot of myself in it right now. I am in a different situation where I have had a few serious relationships in the past, and after being hurt by the end of one, I have turned more inward and have become more interested in developing my own "self". After being connected to others for so long (the past 5 years), I lost who I really was, and developed more as a part of a couple. I understand that your saying this is not what you want.

Honestly, for it to be any kind of serious relationship, that is what happens, whether you like it or not. To the extreme that you stop caring about your individuality and more about the couple is for you to determine. There's no way for you to figure out the extreme that you feel comfortable with until you try a relationship. It somewhat sounds like your not ready to even try that if you're still concerned about your self evolution. Perhaps the next level of individuality for you is a relationship.

What I'm trying to say is you don't know until you try. Seems you've evaluated yourself, perhaps over analyzed. Maybe you should try just doing before you evaluate the situation. That's likely not the kind of person you are (my best friend is that way), but it's just a thought.

As far as talking to women, the best advice I can give is think like your talking to your mother or sister (if you have one). Think about the things that they like to talk about, and the things you can talk to them about. Above all else, don't pretend to be something your not. If you've accomplished something with your life, which it sounds like you have, use that to your advantage and talk about what you do. If what you do bores the girl to death, she probably isn't worth any more of your time anyway.

Another thing about talking to girls: they love to talk about themselves (being one, I know). No girl can deny it. Even the shy ones are more comfotable talking about themselves. So start asking her questions about what she does, who she is, where she is from, what kind of music she likes. Your bound to find something you can talk to her about within those topics. Plus your finding out more about her can help you make a decision: is it worth more of your effort?

I think some people might argue that your opening a door to a cave you don't want to go into (as in they'll talk your ear off about something you couldn't give a crap about). But if friendship is more important first, its best to get to know them this way instead of playing games.

I hope that some of this helps.