I am not the kind of person that likes to be emotional or even remotely discuss emotions.
However, after a awkward conversation, my boyfriend and I decided that we were going to try again. And we are now 2 months into the relationship and I have a feeling that we are going to end like before with me frustrated with my inability to convey my emotions and him being clueless on why I ended up breaking it off.

Basically, I sometimes feel that he ignores me and chooses his friends over me and he has this habit where I don't hear anything from for days and I know that he is not doing anything important that could let that happen.
I never want to bring it up when I talk to him in case it sounds like I am jealous and that is one thing I am definitely not .

There are occasions that I get so angry with him that I finally convince myself that I should talk to him but when I am with him I just don't.
I love when I with him and we are able to have a conversation for hours and hours, but just never about emotions.
I do have to point out that he sometimes tries to talk about it but I automatically dismiss it and change the topic.

Is this relationship doomed to repeat it self and fail? And what can I do to stop that from happening?

So long as you can't find it within yourself to discuss the way you feel and listen to him when he tells you about his feelings,you don't have a healthy relationship.
If there is no honest communication it will fail.
He can't read your mind nor can you read his-start having proper talks or it will not be doomed,but fail from lack of trying.

You need to figure out a way to express how your feelings.

Try writing it down,just for yourself for the moment,keep a journal of your feelings.

When he is doing his thing,you do something with your time...

Both of you should have full lives away from each other.

Start small,say something like... I feel happy that you're here... even if it sounds odd to your ears.. just spit it out... it takes practice..

If you want the relationship to work,your both going to have to communicate how you feel.

If you want to have a life-long relationship with him you are going to have to communicate openly and fully with him. If you can't learn to trust him and open up, the relationship may be doomed down the road. Just try to be yourself and tell him how you feel about things.

Yes this relationship is doomed until you can find a way to express your pleasures and displeasures because there is no such thing as a guy who can read minds.

Stop dismissing your own feelings. Learn to identify and deal with them, so you can express them.