Any question that involves relationships. I'm terrible with my own personal life, and quite frankly, no matter how much you try to change it, I just won't have enough information on the circumstances and the way the parties involved think and feel in order to make a reasonable, well-informed decision on what might work out best for parties involved in either the short-term or the long-term. This is especially true when the only viable solution in my mind involves basically saying that said relationship just doesn't work and that it would be better off for both parties to end it, because it makes me look like an asshole and I don't want to have to deal with the outrage/anger/sadness/blahblahblah.
Kind of along the same lines, I also hate being asked what kind of girl I like. That question is unanswerable. Women cannot be lumped into an overarching category any more than men can under any qualifications other than what kind of genitals they have. People can't be classified in the broad terms that society expects, nay, demands that people be classified under, and it's both insulting and counter-productive to be expected to have a certain "type" of person that I'm looking for in a prospective significant other. After all, I could be classified as a movie buff, gamer, nerd, reader, outdoorsman, writer, otaku, musician, dungeon master, football superfan, liberal, improv comic, dishwasher, and history buff. None of these categories are entirely wrong about who I am, but none of them are entirely right either. I am a person with complex likes and dislikes and complex philosophical, political and moral values that don't exactly work well together but make sense in my head, and I doubt that anyone cannot describe themselves in a similar manner. Why should I be expected to arbitrarily decide what I'm looking for in a possible girlfriend when I can't honestly say it's fair to categorize them into different types?
Wow. That's a huge wall of text, isn't it? Well, to anyone that wastes their time reading what I wasted my time writing, does any of this make sense to you?