Failure at relationships
any girl who's ever liked me has ended up regretting it and any girl i've liked i could never worked up the courage to actually ask her out. whenever i'm trying to be open with them and talk to them about whatever problems they've got, to them it just seems like im nosy and think that they can't handle it themselves. when somebody says that they've got things under control should i just decide not to second guess them and assume that they really do have it under control? i tried that once with a girl i went out with, she had problems cutting her wrists and was also bulemic, all i wanted to do was talk to her and offer to help. well that ended with her going to therapy and her breaking up with me 3 months later when i wouldn't support her decision of her smoking weed. well anyway im not here to talk about that, i just need to know if there's some point in deciding whether to try and help someone or just leave it to them.
this relates to my failure at relationships because it often leads to an argument. a girl that lives across the street from me has been my best friend (and i her's) since we could cross the street. she had a crush on me at one point. i knew she liked me and when i found that out i couldn't have been happier. (ya i know that's the kind of person you want to spend the rest of your ife with when your already really close and then suddenly fall in love with each other simultaneously) but that ended when she decided that since i couldn't be direct with her, (how could i?!?!? best friends since street crossing?!?! what if i didn't want to risk that or was maybe unsure???) and when she decided that i was too "into her buisness". she regretted ever liking me (similar to my ex-girlfriend who also regretted ever liking me) because she too didn't want to risk the friendship.
so this leaves me to ask, is it normal to be unsure about when and when not to help someone? is it also normal to be discouraged about asking out other girls due to previous failures? what can i do for the future?