We spent everyday together (from grade 9 till our last year in College). We lived next door to each other! Our friendship developed and I accidentally fell in love with him. I told him I loved him after two months of dating (we dated in College) and he said he loved me too.
It was a hard relationship though. When I first told him I was feeling something different than friendship…and that I was scared and wasn't sure why I was feeling this way, a girl was interested in him at the same time (a girl that he cared nothing for because she was known for being a gold-digger and sleeping around). He said that this information that I was giving him (about feeling something different than friendship) was something he was going to think about, and that he was going to call off the “date” he was going to give to this other girl (I say the “date” he was going to give to her because she had begged him for chance). The next day he went and slept with her. This hurt me, although I realize that him and I were not dating at all at the time…

Anyway, we got together a few weeks later because it did not work with that girl. He did not care about her, and she did not care for him…but it only ended when she started sleeping with a new guy. I made my move then, when it had ended with that girl. I kissed him one night when we were together, and things bloomed from there. He was happy I did it, because he would never make the first move (he is painfully shy only when it comes to being with women as “more than friends”…so the girl has to make him feel secure).
I know that he never loved her. And it was clear…although he did sleep with her.

He was made fun of A LOT when we were young. He confessed he has a lot of insecurities because of his past (and I can see why because I was a witness to how he was made fun of everyday). He explained that the situation with me was confusing because I was not being clear on whether I liked him by simply saying “I'm feeling different and I don't know how but it's scary”. He said, at least she (the girl he ended up dating) was being very clear so it was safer for him to be with her (he didn't mean physically, but that the other girl was literally telling him “I like you”). He said he knew he was being a immature but it was easier this way.

I knew this deep inside. I know him very well, but it was very frightening for me to tell him I had feelings for him right away, and I tried my best by telling him things like “I'm not sure, but I feel differently…it's something other than friendship…” and I told him “this is the bravest thing I have done” as I too was insecure…it's hard telling your best friend you are in love with them…especially since your relationship was completely plutonic. It was a surprise to me that I began to love him and I was having a hard enough time to deal with it myself, so it was very difficult for me to come out and say it all to him.

So, when our relationship progressed, I felt insecure and angry with him. I felt that he did not know how hurt I was, and that I was just “letting things that hurt me go” because no matter how much I explained the things he would do that hurt me, he would say “I don't understand”.

The problem was he never understood. He would think it wasn't a big deal and I should get over it. He did love me very much and would cry and tell me he wished he could make things better. I knew he loved me…but things wouldn't get better sometimes. Like I initiated sex every single time we were together. And this is not because he didn't want to have sex…but he is too insecure to initiate sex. All in all... I would feel so low sometimes because I would expect that after initiating everything and getting our relationship going, and having to watch him be with a girl that everyone (including him) knew that didn't care about him …would at least try and make me feel special just once by initiating making love, or even kissing.

I became more and more bitter. He left. He said he tried, but didn't know what to do. I miss him so much, and I love him. I realize my anger was consuming me. I still know that I deserved at least a boyfriend that was not too shy to kiss me, or tell me that I was pretty (he never once told me anything like that because he's too shy to tell girls this). But at the same time, I know that even though he was the way he was…the treatment he got from my frustrations was far worse than anything he was doing to me.

I miss him so much. I went after him for a few months and told him I loved him... he was surprised at me being so caring because due to my bitterness I had stopped being the loving woman I was (am). I told him I realize the way he is and I realized how horrible I treated him as a result. In fact, I have to admit, I became so horrible that I cannot even recognize the person I became while him and I dated; cold, spiteful, and again, so abusive verbally and emotionally.
He has fallen out of love with me (rightfully so). Two years ago he moved to work for his brother's company, and I've only seen him three times since…but these past 9 months I have not seen him at all. He called a lot at first, but these past three months, since he has found a new girlfriend, he has only talked to me twice…once to tell me about a fight they had had.
I miss him dearly. I pray to God that we should find our way back to each other. Most days I am fine now…but even on days that I am very fine and know I can live without him, he is still on my mind. That's it. He is always on my mind.

I also notice that when I pray for him to come back or dream about him coming back, every time I think this way, I've been picturing him saying or doing things that he in fact “never” says or does. …Like him holding me without me coaxing or prepping him first. This scares me a bit…because I wonder if I am loving something I know he could be, but isn't. I mean, I could always see how much he loved me, did for me, cried for me, etc, but there were things missing (as I mentioned earlier about his insecurities getting in the way).
Anyway, this sounds like an “odd” situation. But the end of it all is that he is not in love with me anymore... at all…and he has told me that he cares about me but completely as a friend time and time again. I have not dared to try for him anymore because I want to respect him. And sometimes this is killing me. I wish someone could give me a magic potion so I could get my best friend back. I know we could have a loving relationship. I wish we were cured of our childhood insecurities so we could make it work. How do I go on without him? I am getting better and stronger, but almost every day I crave to go for walks again with my best friend, to hold his hand down by the path near the street we use to live. How do I erase these memories (even though I don't want to because they're all I have of him)?
What should I do? I've read other posts, and it seems as though there is nothing I can do but live my life. It's so hard. I believe that even if one day he realizes that him and I are meant to be together, he will feel too insecure to approach me and to tell me he loves me; this thought scares me.

He was your first love.

Now it's time for a second.

It'll take some time. BUT a new "friend" will find you when you least expect it... the more active you are, the more likely to find a new friend, that may think of you as... more than a friend. Lucky them (and you!)

Ps - if you read in between the lines of your post i think you know you weren't a perfect match with him - but love yells louder than practicality we all know - so listen to that voice when you are calm and respect it.

Deep down inside, I think you already know the answer to your own question.
Live and learn from mistakes, that is how we grow.

A strange update. After not hearing from him for a while, I checked my email and he has sent me a long letter about what he has been up to. He is still with his girlfriend and they are planning on going to Europe in September for vacation. For some reason I am not very hurt that he has a girlfriend... I'm not sure why but that doesn't bother me.
But it does bother me that he is not in love with me anymore. Even so, I'm at least thankful that he wants to be friends.

I think you've fallen into the classic trap of wanting what you can't have. It's human nature to feel this way, as something is always more appealing when it's unavailable. As Ash has suggested, it's fairly easy to "read between the lines" of your post. It seems that the two of you were really not compatible, that you had different expectations of what should be. It's not that either one of you is right or wrong but basic compatibility is essential for a relationship to be successful. It sounds like you and he are just too different to be able to have the kind of relationship you want.

You may have wanted this a lot more than he did, and still it couldn't work, so time to move on with your life

Go back and re-read your original post but replace you with a female friend and I think you will see that this guy has way too many insecurities and issues to work with you or about anyone. My bet would be if he suddenly told you how crazy he was about you and never wanted to be apart , you'd feel great for about a week then realize you were only attracted to his unattainability, not the real him which is insecure and needy. And if I'm being honest here, it doesn't sound like he was that great of a friend either. Sorry to be harsh but move on and maybe you can be casual friends when you have had time to heal fully.

We often fall in love with a memory, or it is often to want something we know than have to face the unknown.

I am sorry for all the pain you will have to go though, but I am sure you will grow and find someone new.