How can I learn to care about people (and I guess including women?)

[Thenewguy]

To keep it short, I have trouble connecting with people deeply. Most of my male/female friends, we are really cool, we can laugh around each other, text each other, enjoy each other's company but I don't feel a deep sense of connectivity with them, if they suddenly went away tomorrow, I feel wouldn't care. This is true even for my CLOSE friends, where we actually know a lot about each other.

I know in order to have a good conversation with someone and connect with them, you have to actually have curiosity about them as a person and want to get into their lives. But when talking people, besides the laughter and random jokes/flirting. I GENUINELY do not care about their deeper lives (or even a lot of things lower then that) enough to ask about it. This is true even for my parents, who I actually love and like as people and don't have animosity towards them.

I tell myself "You should ask them to get more deeper with what they said, then possibly relate or just let them talk " And sometimes I would, just because I know it would cause a better connection. But I don't actually CARE, even though I feel I should. So most of the time I won't, just because I don't want to be inauthentic.

I remember mark mentioning somewhere about how I should like women (in the do you like women thread) just for the sake of them and how they are and not what they can offer. and I WANT to, I really do, with everyone. and it's not that I DISLIKE women, it's just that I don't care about getting into their lives like that (not just women, all people) for no reason unless they do something that makes me interested, which is rare.

So how can I learn to care about people's lives and have a genuine natural curiosity?

[Alvar]

Good question. I feel like your post could almost have been written by me.
In fact, I have been asking myself the same question. Here's some of the answers I've got to the question of What if I "give" a little bit more of myself to those close to me:
I’ll have a lot of work
I’ll create expectations
I’ll have trouble managing my downtime and my space
they’ll invade my space and I won’t know how to assert myself
I’ll spend my time with others rather than by myself
they take the hand and the arm
they get to know me and make fun of me

I feel these answers are not going deep enough, so I am looking to explore it further.
These beliefs and assumed responses come from my early years when I was lonely, naive, very introverted, was taken advantage of whenever I dared to open myself or assumed fault whenever things didn't go as I expected. They're mostly defence mechanisms that served me well when I was young and didn't have much skills but are pulling be back now that I can assert myself and am more confident in my relationships.