I take a certain pleasure in asking people difficult "would you rather" questions that they aren't entirely comfortable even thinking about, let alone making a choice. For example, I'd ask a woman whether in the direst of circumstances, she'd rather have sex with her brother or her dad. Yes, it's fucked up. It's supposed to be.
Another would be to ask a mother of two, if she had to choose, which child she'd save and which one she'd let die.
I'm not sure what questions like this would pose difficulty to me. It probably wouldn't be family related, because--while I like my family--there are certain irrevocable distances when half your sibs are an entire generation older than you. I have a nephew as old as my cousin.
So, dear readers, in the end, the toughest choice would probably be something stupidly material, like whether I'd ditch my PS2 or my laptop. Actually, that's not even a competition, because my laptop is so much more multifunctional than my PS2. Both are entertaining, but a PC opens many, many more doors of entertainment and stimulation.
Thus, I pose it to you. Find a question I'm not comfortable answering, be it a "would you rather" or something else entirely. Make me sweat, people!