While the hesitating and questioning can be hugely detrimental (and I am sorry that you have to deal with that, I know the feeling) sometimes I really wish more people did it, at least to some extent. One of my flatmates has absolutely no clue how obnoxious he can be sometimes and it's irritiating as all hell.
More than anything, I appreciate being judged. But I really don't mean judged, what I mean is I wish people were open with their opinions of me, and told me, so that I could improve myself. Not for them, or to impress anyone, but to make myself a better person.. for myself. And sure, being a better friend or getting rid of shitty personality traits resulting in people liking me isn't so bad either. How was your flatmate being obnoxious?