Hello friends,

I am 26 years old. I've had one girlfriend, been with 2 women that I myself have physically escalated into bed with, and that's it. I maintain a very healthy meditation practice, and have even considered completely abandoning all signs of pickup because I wanted to take that (the meditation) to an extreme.

And so, here I am now, I've been going to therapy, and I am beginning to come out of my shell, and I can feel the desire to get back into this come back full force. Because now I think that it doesn't really matter so much to the point where I have to restrict my entire life to 1 or 2 things, I think that it is completely OK, to continue to work on my practice, and 2) to also try to talk to women on the side.

What is it that you would tell me, as someone who has only approached a few women in his life, and wants to learn how to have conversations anywhere, and to be able to find or maintain relationships with relative ease ? I am in general a little bit shy, I think I do have my moments, but from the standpoint of just sitting with whatever it is that I'm feeling, and just owning up to that and acting on that, I think that I am a bit on the shallower end of the scale. It's not really that I can't have a conversation with anyone, but I think that I am just pretty neurotic about said conversations, and it always seems like I'm stuck in this shell.

I kind of know what to expect, but everything just seems to be so much. I am considering trying to go out on week nights and stuff to take this seriously, but how would I begin ?

I have no job, so I can't really go to any clubs or anything. I also don't really drink, and I live an hour away from said pickup locations (NYC), so it can be sort of a drag to actually go out, and expecting so little results. It just feels so daunting, and so much of a commitment, but I am not sure if I can even enjoy my night if I go because I haven't proven yet to myself that I can.