How happy (or sad) are you as a lone wolf?

I just turned 30.

I've been a lone wolf the majority of my life. I moved out on my own when I was 16 years old. I sold a ton of pot and everyone in my small town knew me, and I knew everyone. Parties. Girls. So on and so forth. When I was 20, I ditched my home town of 19 years and moved to somewhere which I knew nobody. It was rough at first. I saw a few girls during that period, and went to a few parties. Made some friends. But drifted towards going solo. It is when I began finding comfort hitting a restaurant, movie, etc alone.

Then at 23 I took 4 months and drove around the country with my guitar and dog. It was... uplifting to say the least. The freedom of not having to worry about, care about, help, satisfy, etc. another human being was quite nice. This was to start my second major life move. These moves began to become normal things for me. The first was Oregon, then Florida, then Texas, then California, then China, then another part of California, then another... I haven't had a girlfriend since and while I'm very personable, kid fellow who people tend to like, I generally don't hang out with people except for those traveling to visit me (I'm in a major tourist destination with high hotel rates. Crashing with me for free causes 6-9 visits from people annually). I'll hook up with a long distance friend here and there, or possibly an occasional random hook up or go get a massage to get the chemicals released. I am a man, and I've always had needs that should be taken care of at least periodically.

I've been completely content with this. I've experienced a lot that others do not in their 20's. I've been very successful in business, and now have the ability to go to one of the top universities in America without any form of assistance from other people. I'll get comments from people along the lines of "Wow, that drunk midget should write an autobiography" or "drunk midget knows whats up. Dude can get shit done" or other such flattering things. On the surface, its all good, and underneath it really has been for the most part.

However, something recently inside of me has died. Or perhaps something has grown. I am unsure. But I find myself feeling lonely. I'm having trouble acting on any FWB or fling sexual encounters. Instead, I have this urge to connect with one woman. I want someone to care for, and someone who will take care of me in return. I want to cuddle as I fall asleep. I want to have someone who I can strive to be a better man for even if just to make smile. I'm full of these hopeless romantic thoughts. I've always been a softy, but none of this. It's more like "Oh, Shiela needs a place to crash while in town. I totally know Sheila is dtf. I'll do something nice and romantic for her, so she really enjoys getting boned". That kind of romance. Nothing real.

The problem with these feelings I have been having for the last few months is that since I have been a lone wolf the vast majority of my adult life, I no longer am capable of playing the game to get women. You know... the game. I hate that shit. Being a lone wolf, you can be 100% honest 100% of the time. Cuz at the end of the day, who cares if this chick likes you. You are more than happy going home alone and never seeing her again if she doesn't like the truth. This doesn't work so well when you are actually wanting a permanent lover. For me, I'm such a caring guy that my honest feelings for women are seemingly too strong too early (people equate caring for someone to be falling in love with them, which I don't believe is true. I can have a crush on a girl and care about her well being and treat her as well as a dude who was in love with her. She deserves to be treated that well, whether I'm in love or just interested. That's my personality). I've always treated women this way since adulthood, but when not at all interested in a relationshipsuch behavior just leads to a quick hookup or becoming friends. I also find that my urge to care for someone has leaked into caring for EVERYONE. Like, I want to help everyone and make everyone happy. Possibly its a subconscious thing which I want it reciprocated. Possibly it is a direct reflection of my desire to have someone to care for, and since I do not it goes out to everyone and anyone who is nice.

tl;dr what I am getting at here is that the only constant is change. Sometimes what makes us happy will later make us sad. In my case, my lone wolf mind set made me happy for about a decade until something inside me changed. Now that lone wolfness makes me sad, as I almost feel trapped in it as my desires have changed and my personality has not. My freedom has become my enslavement.

/r/AskMen Thread