After clicking around your comment history and blog for a bit... I see you grew up and live in Indy -- I did as well until I moved to Chicago earlier this year, and we're around the same age (I'm 30). Some of what you've written definitely reminds me of myself years ago.
My (admittedly incomplete) impression of you is that you seem smart, but that you've got a lot of strong beliefs about things that don't seem to be working that well for you. I'm not sure I have any advice for that, but in my life I've found that my beliefs and values have changed and shifted over time. Usually those changes were started by external circumstances, followed by me choosing to let go of beliefs I was emotionally invested in (definitely not easy).
An example: I used to hold a pretty dim view of people, but I have changed this view over time and now see that most people are a mix of good and bad. The catalyst here was just trying to adjust my belief to be accurate -- people do a lot of good (in addition to the bad), and I couldn't square that with my existing belief that people were basically bad.
Probably the biggest external circumstance that forced me to change many beliefs was getting married, which will probably be unrelatable to you, but I'll try to relate it to you anyways: Getting into a romantic relationship changed my priorities because of the way it made me feel, and how all of a sudden I felt I had someone to really live for and strive to help in a way that I had never even really felt about myself. Things that previously seemed insignificant all of a sudden felt extremely significant. E.g. getting a better job, because I wanted to better provide.
Dating tips? Learn to filter -- go on as many dates as you can and figure out what kind of people you really work with. If you only go on one date every 6 months, you're not going to be able to figure out what it is that you really want in a partner. You might be able to do the same to find platonic friends? I haven't had a group of guys that I hang out with since high school, but my SO fulfills the friendship role mostly, and I'm too busy to even try right now.