Relationships As We Get Older

Currently I'm trying to strengthen a friendship that has been strained due to multiple reasons (distance, non-communication, basic social retardation).  I had a pretty good conversation with that person over a few hour period and began working through a lot of core issues we had.  I felt like we broke a lot of ground and we have a lot of potential to kickstart an era where we get along much of the time and actually connect.

After reaching out a couple of times in the last 10 days, I finally put my pride to the side and got blunt on the last voicemail I left. I said, "I've been waiting patiently by th phone for you to call me back.  So, yes, I want you to call me.  Call me.  Call me. Call me. Call me. I want to talk to you."  I think the time for hinting heavily is over in this relationship.  I have to be blunt until we have an lexicon of understanding between us where subtlety can be used.

I feel a bit juvenile in my train of thinking ("Oh, that person should know what I mean") but I realized that many of us are not used to having to work a bit harder to maintain/build relationships. We can't read each other's minds and some people aren't as sensitive as I am in reading into things. 

It got me thinking about my own issues with making new friends as of late.  I still have practically 0 male friends in Chicago.  I've reached out a few times to a few people but it seems that I can't do much follow up.  Perhaps it's the alpha-male in me not wanting to compete with others or just ineptitude in making connections with guys.  I'd like to have more male friends but not sure as to how to a) make them and b) foster them into viable connections. 

Perhaps I need to find new male friends who can be just as candid and blunt as I am with my old ones :)