I have a really big problem. I've been with my boyfriend for almost 2 years now and I've never really warmed to his brother, and vice versa. It's got to the point now that whenever we're going to go see him I just dread it and it's really awkward. Another part of the problem is I really don't know what to talk to him about and probably vice versa as well. Do you think I need to do something drastic, like if I'm ever alone with him give this kind of speech: "I know we've never really warmed to each other, I really want this thing with your brother to work, and I really want to be able to get to know you. Would you be up for maybe hanging out alone one day or something?"
If you don't get along with him, you don't have to. Avoid him as much as you can. You don't have to force yourself to like him. You don't have to force yourself to talk to him when the two of you have nothing to talk about. When your boyfriend goes to see his brother, why do you feel you have to accompany him?
Avoidance only works as a temporary solution to a situation like this where the boyfriend or girlfriend has a high chance of being your spouse. I'd say you're in the right track OP, does your partner know the situation?
You have the wrong idea of the meaning of avoidance. Avoidance is when you refrain from doing things that are necessary. She is not going to get married to her boyfriend's brother. What is with this American obsession that you have to force yourself to get along with people who are technically family but incompatible with you? How about thinking outside of your box for a change?
It's not an obsession, because it stems from the very real situations in where family gatherings happen which forces people who don't like each other to be in close proximity together...if you skip out on the gathering it can strain the other relationships.
I can't stand my fiancés brother most the time. He has always cheated my fiancé out of so many good things, treated him like absolute crap and I just can't respect anyone who does that. Luckily, my fiancé doesn't blame me. I've never had words with his brother, in fact he thinks we're cool but the truth is I just act politely to keep the peace in the family. I can get my man worked up very easily by complaining about his brother and how unfairly he acts toward my man. But I avoid doing this the great majority of time, because it just creates more animosity between them. They're brothers, things have come to blows between them many times. With that said, I don't actively try to mend their relationship - thats their business. If my fiancé comes to me with an issue he wants to discuss I give him my honest opinion and usually encourage him to take the high road. Pitting him against his brother will only create issues imho. Chances are you don't like the brother for a reason. Those reasons are unlikely to change but it really doesn't hurt to be polite and let things develop naturally as things do. Remain civil, but you certainly do not have to like him. This situation can be a trial of your patience and maturity.
Sounds rough, how do you plan on enduring this for decades? I still stand by my original assertion that this is hard to do and never gets to the root of the issue. It is just a coping strategy.
My advice would be to first bring it up with your BF, but be very careful and tactful as to how you do it as you don't want to put him in the middle of things. But be honest with him and mention that things are okay with his brother. It may be there's nothing he or you can do, but it's better than sitting there in stir when your face to face with his brother. But there again when you're with his brother if it gets weird, then sure you can confront him and ask what the deal is, but be prepared if you do he may give you a mouth full. Unless the guy is a total ass my assumption is he has some issue with you or probably thinks you aren't good for his brother for some reason and just hasn't expressed why, so if you open the door for him just be prepared for that.