Question

I feel silly for asking this, and because I'm using my phone I can't really write a big long post (which is probably lucky for yall because I tend to carry on). But I'm going to ask it because it's bugging me and I feel too uncomfortable talking about these things with anyone in person. But basically, how do you know when you like someone? I'm so used to blocking out feelings because 1. I've never had a relationship due to abuse to myself and most of my female relatives, 2. I've always been so convinced that nobody likes me that I blocked feelings to avoid feelings of rejection, and 3. Because I feel so uncomfortable with myself that the thought of me with someone and all that intimacy makes my skin crawl. But recently I've come to realise that I've done this for so long (literally years) that I have got to the point I can no longer see the difference between liking someone, feeling envy when someone else likes another person and not me, and just hoping someone will like me so that I feel wanted. For example one of my friends, I thought I liked. But he was in love with someone else, though he adamantly denied it. But everyone, including myself, thought he liked me. Then when I confronted him, he said that he had absolutely no idea what I was talking about. So I told everyone I didnt like him, looked for every flaw I could to convince myself I didn't like him, and now I don't like him and I wonder if I was just hoping he liked me and had envy with everyone else he have attention to. Now there is someone that I'm friends with who is about as decent as they come, and I thought I liked him. But I didn't think he liked me so I determined that I in fact did not like him and some dreamier better guy will come along. Then last week his step sister let it skip that he did in fact like me (she said she thought I already knew), but that he has said he doesn't anymore. But she thinks he is lying. So now I've been thinking about him again. But I don't know if it's just because I want him to like me or because I like him. I am a few years older than him and all his female friends are on him like leeches (though he's not one to take advantage of that). I am really confused as to what I am or am not feeling. And I feel like a 15 year old while I write this! Sorry I have written it so confusingly, like I said I'm writing this on my phone so it's going to take too long to write a more detailed story.

Would you be comfortable being honest and telling him you like him. Even if he rejects the idea, he will most likely handle it nicely and you can still be friends. Its good you go for the decent nice guys.

If you want to get to know someone better, you approach them and talk to them, get to actually know them better; liking/disliking isn't a thought process, you can't "decide" you like someone or they like you, it's an actual process based on in-person experience with the other and knowing yourself and what you like and dislike. If you feel good when you are actually around that person, you want to be with that person, want that person as a friend. If you are uncomfortable around a person, do not want to be around that person feeling those feelings, then you do not have that person as a friend.

Once you get to know a person a bit, see that you make one another feel good and enjoy each other's company then you can take it to the next step, see if you would enjoy a deeper, more intimate relationship with each other. But it is always a two-person job, it's the actual interaction and communication which is important, not what one thinks is going on. What we think needs checking with reality, especially if it is about another person. Only another person can tell us what they think and feel.

It's not so much about deciding if I like him or not, it's more about interpreting different feelings and understanding the difference because I'm so used to building a wall and blocking/denying feelings. I've got myself in a bit of a rut where I've let it get so out of hand that I can't understand these feelings anymore.
A few months ago I went out to dinner with this friend and we spend hours talking and talking, I went home thinking he was absolutely amazing. But then I got myself into this idea that he doesn't like me, and that my 'feelings' were just because the idea was nice or I wanted him to like me or SOMETHING. Then I became adamant that though he is a very nice guy and very decent, I don't like him as more than a friend. Then as I said his sister during a conversation started talking about how he's been thinking about me in the past, thinking I was already aware of it. Now it's been on my mind for over a week, and I don't know if I just like the idea that someone likes me, or I'm flattered because so many girls are all over him and he chose me, or if I really like him and won't allow myself to admit that.

I know what I'm saying is confusing, I'm confusing myself just talking about it! haha

And no I couldn't tell him, I nearly did that with another guy and got totally rejected.
But this guy is a really great guy, he has good morals, a diploma, a job, we have a ridiculous amount in common (including very similar childhoods).