It is troublesome creating a war between my head and heart. I fall asleep restless and light. What happened? I should not create screenplays in my head or fights with invisible people. I ought to let go, correct?

I spent a couple days with Sean and his mother. He needs help buying a car. I know he is more than capable of doing that on his own; however, the state of Rosalie's wellness is creating a burden on him. He is unsure how much longer she will live. He remarks that he is "screwed when she dies," and needs help looking for a place and buying a car. He hates asking for help. Moreover, he asked if I could do him a favor.

One day I was at his place, talking and catching up. He was bored, and said he missed me. I told him (before I left) that my mom would be sending me money that is well over $12,000.

The next day we were talking, and he asked if I could help him out. I know him well; I know it is difficult for him to ask favors. I know he is sincere when he said I am the only one he can trust.

I will be giving him money to buy a car.

I do not want any of my friends or family know about this. I do not mind if he told his family or friends what I am doing--I care less of what they think. Moreover, it is not that I care what my "friends" or family thinks- it is that I depend on them now, and I absolutely do not want questioning or talk going on behind my back. Since they are close--I cannot deal with it and I live with two of them. I already feel a strain with Kristene and Mike. I have this nagging feeling that they are pretty close to kicking me out, talking about my faults and actions, and are annoyed by me.

Therefore, what is possibly going on between my head and heart?
Well, I believe it is not my heart; it is something else that I cannot place my tiny finger on. Fear, perhaps? Insecurity? Well, let us see.
I am afraid/insecure that I am being used for money. Not my friendship. It will not be the first time he has been nice to someone to obtain some cash (from his father).
Let me say that I do not blame him or his brother being amiable toward their dad for a while. Their father left them when they were young. He played around with different women and was abusive. When their father walked back into their life, he offered them money, plenty of money, if they had him stay at their/our place for the remainder of his project. When he left, he stole their things. Sean wanted them back, and for a while, believed his father really is a good person who does love them. Therefore, he played nice. He called him, asked for his things back, oh, and let us not forget the cash. Their father did not contact them, again.
That has been the only time since I have known Sean for doing that. I believe I am in a similar position at the moment with my biological father (it's awkward saying sweet things to a man whom I had ill memories of. I do not say sweet things to him as much as he does to me. It's funny how he can say them without raising me. He possibly thinks I do not remember the things he has done to my mom.). I will be amiable towards him when he shows he does care and is sorry for not being there.

This is when I start to rationalize between my head and "heart."

1. Sean asked to be friends first before knowing about the money. He showed courtesy and amiableness towards me.
2. I know when he is being sincere.
3. I know he does not trust anyone. The years we spent together developed a trust I know is difficult for him to develop with others.
4. He has been kind and patient towards me when I had to vent or cry. He knows how to calm me.
5. I know him; and it surpasses the doubt or fear I had in the beginning.
   

Now, I know I can trust him; however, can I trust myself to the vulnerability I am opening myself to?
I believe that is the real war between my head and heart.