For as long as I can remember, I think there's been something about me that's a blessing and a curse.

All the way back to high school through now as I'm in my mid-thirties, I feel like I've gotten along better with women than I have with men.

It's not that I don't like or have guy friends, but it has always kind of been weird and borderline uncomfortable for me that when you get guys together, everything becomes a bit of a competition, no one wants to have deep talks, all sorts of things. I just feel more comfortable with women friends who are in better touch with their heads, are more sympathetic, more caring, etc.

The flip side of this is that I've never been able to move beyond kind of a "big / little brother" relationship dynamic that I have with anyone. Most of the time I am more than happy to remain totally platonic buddies with a woman because we get along great and I wouldn't want to mess up having a good friend because things got messy with a deeper relationship. But sometimes there's times when I do feel a bit of a connection with someone and want something deeper, but I get it communicated to me one way or another that they wouldn't want that.

There was a time before I started working on this with a great therapist that I was feeling frustrated in ways that weren't good for me or anyone else. I'd see women that I either did or didn't know and would get resentful of the guys that did get their attention or get irrationally angry in that I saw their kindness or hotness and think that I was undeserving of that in a more intimate relationship kind of aspect.

I'm way better about that, but I still have a lot of tie-ups. I feel like I'm a halfway decent looking guy and I am pretty sure that I can be charming and fun, but the longer that stuff like this goes on, the more that it gets in my head and erodes my confidence. The more that women just treat me like a brother or best friend, I think I find subconsciously somehow that I stop putting in a lot of effort in my appearance or methods to really attract anyone otherwise because it just feels like I'm continuing to push the boulder uphill with a useless effort.

The reality of the situation is starting to hit me hard too. The older I get, the more that the pool of available people (or at least people without significant baggage) gets way smaller. The more that time goes on, the more that I'm starting to face the fact that I may be on my own forever and that the only female companionship I'll ever have are those kind of "bro" relationships.

I think that realization is settling in more in that I'm kind of learning to stop looking and stop trying. I want to stop focusing on it entirely so I stop distressing and depressing myself, but it still eats away at me for the time being. I think I used to be bitter about it, but I've at least been able to work with my therapist and on my own with being okay about it. My emotions have moved on from being kind of jealous and resentful to just being more of a self-doubt. At least it's an improvement.

TLDR - I have a lot of trouble finding ways to make women see me more than a best friend or brother type. I'm more than fine with that in just about all cases, but I am just at a total loss as to how to develop a real relationship with anyone beyond that. I feel like I'll never be seen that way and frankly I'm starting to realize I may need to give up on trying. Does anyone have any advice for me in my situation?

Hey everyone, thanks for all the great advice. I had an update here: https://old.reddit.com/r/self/comments/1d7ex5i/update_i_37m_am_a_little_exhausted_of_always/ ?