The best part about loved ones making bad decisions is that they are going to be the ones that have to live with it, not you. Although you are close to this person, you get the advantage of getting to be there for the other person, but you're not going to have to be affected by that decision each and every moment of your life like your brother will. If it really is a bad decision, he'll either learn to live with it and make it work, or change his mind.
And yeah, you cannot 100% judge how bad a relationship is sometimes because close friends and relatives can often just hear about the bad things (hey! that's what friends are for) but they don't really see how things are behind closed doors.
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