Believe it or not, but this is something that almost everyone goes through. Of course, this might be more extreme than is normal, but everyone feels insecure like this to some degree. My best advice is to find a good hobby and take things easy. This will pull your mind away from your problems until you realize that the problems are not as big as you thought they were, and your life will become more manageable. Just find something that you really like doing, and if you don't know what you like just keep trying new things, learn an instrument, take up horseback riding, learn to cook, take up a sport. Once you find something you love, stick with it and it will keep you occupied. Meanwhile just relax and take it slow, and once you feel comfortable you need to tell this person how you feel. I am sure that they care about you, and deep down everybody wants to help someone. If you tell them nicely, they will be glad to help you in whatever way they can.
Hey, I am assuming you are still very young, just because you said something about school. I just wanted to let you know, I know how you feel, a lot of what you wrote I have felt before and sometimes still struggle today with it. Don't know if you have gone to a DR. or not, I have been to LOTS, and started later in life than it should have. I didn't start going to DR until i was 29 and I am now almost 35. I was told Major Depression, then Depression, then Adult ADD then BPD, Who knows, all I know is I feel better now without taking meds. Again, don't know if you have or take meds. I suffer from not taking the ADD meds, but that is it. Anyways, I just wanted to let you know, I know how you feel with wanting to please everyone and you are not happy with yourself or happy in general unless you know others are happy with you. Like I said, I am almost 35 nad still struggle with that to this day, not so much as I used to. But, still more than I want. I worry too about if this person is happy with me today or not. When I walk into my friends work and she doesn't seem too pleasant today, I think what the hell did I do, to make her so distant with me. But, the truth is that is when you need to step back and realize did you do something and I find that the answer for myself after I go around it, is that I did NOTHING, sometimes I haven't even seen her in a couple days, so I know I haven't done anything. Sometimes , that is just how people deal with what ever is goin on in their life, and we take it the wrong way because we are constantly seeking acceptance from others so that we can accept ourselves. I am agreeing with Martzy up above, find something you enjoy and are good at that way you can begin on accepting yourself and be happy with yourself and stop worrying about making others happy with you. Because in the end, you are with you and you need to be happy. Others will not always be around, but you will always be around yourself. Anyways, got to run! :)