Overcompensating for a lack of sociality with $.

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Does anyone else have this problem?

For the longest time I have struggled with keeping, and properly managing friendships. I feel like the only way for me to keep any sort of social contact with anyone is to do favors for them. For the past few years, I have kept very little company, and the only time I see these people is when I am giving them rides to and from places, or buying them food or beer. It's like I overcompensate for my lack of social skills by buying them things and showing them I can help out if needed. So many times I have found myself in financial hell because I've spent all my money, or lent hundreds up to thousands of dollars, trying to please other people, because it's difficult to please them otherwise.

Even today I will see the potential for some random social engagement, and I will attempt to plan out what I should say beforehand. I will go over the words in my head. In my mind it all seems rather sophisticated, and with a decent vocabulary (not unlike my writing style), but most times when I try to deliver the actual message verbally it comes out garbled with stutters, abrupt pauses, and I get immediately overwhelmed, causing me to essentially escape whatever social situation I'm currently in. My roommates must think I'm so weird, like all my previous roommates.

Zaecharia, I always took the opposite approach. Some of my earliest memories involve my parents threatening to throw me out of their house, and telling me I wasn't worth taking care of. As a result, I always saved every dime I could get my hands on, thinking I might have to take care of myself. I've known since I was seven or eight years old that I couldn't count on anybody but myself. Since I had problems doing well on jobs, and since I didn't get along well with others, I wanted to put myself into a position where I could be self-sufficient, and tell the rest of the world to go to hell. Now, I am in that position, and the only people in my life are those who can accept me for who I am.

Thelibrarian

I did just that when I was 17. I ran away to get away from my parents, emancipated myself, and worked two jobs to pay the bills. My parents threatened to put me in homes and institutions when I was growing up because they didn't know how to get through to me (but they never thought of a psych evaluation!! !).

When I was a teenager I was at an impass. I could either go out and spend time with "friends" or stay home with an abusive family that only caused pain, many times physical pain. If I was dealing with abuse at home, which was almost a daily occurrence, I would try to leave the house for as long as possible. Most of the time I would just go hiking alone, but if there were other people involved it was usually the same one person, who I usually bribed with "gas money", and whoever he was hanging out with at the time. Depending on who he had with him, it would usually end up with me quietly observing while he was interacting with them.
I could tell something wasn't right.

I appealed to the two friends who helped me with what I now suspect was a special interest of mine: playing and writing music.

The thing is, when I was with these people, I didn't participate the way everyone else did. They would ask me a question and my response would be short, careful, or non-existent. A lot of the times I would end up being teased by those I thought were my friends for my awkwardness, my difficulty speaking, and my dislike of being touched. (that was a big one for them, they would gang up on me and grab at my sides until I was in a full on rage, which didn't take long.
(I took seven years of mixed martial arts though, so they got at least some retribution.)

I currently share your feelings of not being able to count on anybody. In the past I thought there were friends I could count on, but a lot of the time it turned out I was being played in some way (without me realizing it until much later).

I have a friend like that, unfortunately she is infatuated with someone very manipulative who skilfully takes advantage of her generosity.

Sadly. My mother was that kind of person. I think that the only friends that she ever had where the one's that she paid.

Rich people always have friends.

I was like this since early childhood; the neighborhood children would always come to my house to play with my "cool" toys, though very few of them seemed to actually like me as a person.

This is the only ways I have ever known to be liked by other people. Fortunately, I do get a bit of joy from the happiness of others, so I suppose that it's a symbiotic relationship.

I was rather poor growing up, so I didn't even have that as a child. I was pawned off onto my brother who was a year older than me, and was forced to spend time with him and his friends, who loved to bully me and give me a very hard time. It wasn't until I got a job in high school and started spending copius amounts of money on video gaming that I miraculously obtained those types of "friends", who would only come over for that reason.
I think a lot of people have friends like that though, but a lot less people ONLY have friends like that.