She: Do these pants make my butt look big?
He: I don’t like 'em. Take 'em off, now! Ah, that’s better.
Bingo. Like animals can smell fear, all the women I’ve been involved with can smell equivocation a mile away. Take that dreaded question, “What are you thinking?”: Seems innocent enough, right? You want to tell yourself that she just notices you being a little quiet, maybe your brow was furrowed a bit, and for all she knows, you could be mentally wrangling with a really tough crossword puzzle clue. Yeah, we’d love to believe that, but we know damn well she saw our eyes linger a picosecond too long on her best friend’s most deliciously tight ass, and now we’re in the hot seat. One way or another, she’s going to get it out. If you stonewall, you just make things worse, because she knows you’re lying, and you’ll look even more guilty.
If a woman has to ask you if you think she’s pretty or hot, then she’s probably too stupid to work out that if she doesn’t know by now whether you do or not, then the amswer is probably “No.”
As for the “Does my butt look big?” question, I’m with the women who really want to know. Assuming that I am moderately aware of my defects, I’d rather other people were kept unaware of them as much as possible, so if my butt DOES look big in this, I’ll change into something more flattering. And I won’t be too thrilled with you if you say it looks good and everyone who sees me wonders why on earth I’m wearing something that makes my butt look big!
This thread is reminding me of a conversation I saw on a rerun of That 70’s Show last night.
Eric: Do I need to check with you before I go out with my friends?
Donna: Yes. No. Sometimes.
Eric: How will I know which times?
Donna: You’ll know when I get mad afterwards.
Eric: Okay…is there maybe a better system than that?
So, what are you doing Saturday night? 
To sort-of reply to the OP, I usually just tell them I know its a trick question an I won’t answer it. This frustrates them and usually gets me off the hook, because I caught them setting a verbal trap. Of course, I usually spontaneously compliment their looks and other attributes as well, so its not like I’m being an ass.
She: “Does this make my butt look big?”
Me: “It sure as hell better! Get over here so I can have a closer look” [and maybe a squeeze too…] 
Ranchoth, CynicalGabe – trying to get invited to check out my butt?
I get the urge to ask these types of questions. Usually I’m feeling lonely or neglected, and I want attention.
I try to avoid doing it because it’s immature and annoying. They sneak out sometimes, though.
I have a friend who, when in college, had the habit of getting drunk and asking “am I cute?” over and over. I, also drunk, would answer “not when you ask if you are” and she would cry.
When I ask ‘how do I look’ I’m usually looking for things like “fine, but the underwear goes on the inside” or “is that barbecue or chocolate on the front of that shirt?”
Blatantly.
All I ever want to know when I ask about how clothes look is if they look stupid on me. I don’t disguise this as “Do I look fat in these pants?” Trust me. I know the answer to that already.
M’dear, sight unseen, I can already assure you that you have all the graceful Callipygian curves of the harvest moon. But it is your wit and disdain for the pointless savoir vivre that kindle the sky light that burns unrivaled in the cold and inky night of existance.
So, how’d I do?
Put me in the “what the hell is wrong with women like that?” club. I would never ask a guy if he thought I was fat/ugly/looked good in these jeans. I’m of the mindset that, if a guy shows interest in me, obviously he thinks I’m attractive. Sure, compliments are always nice, but I’m secure enough with myself that I don’t feel the need to go fishing for them. If I want an honest answer on my choice of clothes, then I’ll ask one of my girl friends!
I seldom have to go to a dictionary, even around here, but I had to look that word up. I like that word! Thanks, Ranchoth!
Main Entry: cal·li·pyg·ian
Pronunciation: "ka-l&-'pi-j(E-)&n
Variant(s): or cal·li·py·gous /-'pI-g&s/
Function: adjective
Etymology: Greek kallipygos, from kalli- + pygE buttocks
: having shapely buttocks
“Why no, honey, those jeans don’t make your butt look big. It’s the Haagendaz and french fries that make your butt look big.”
Asking a question when you already know the answer is emotional agression.
Tris
“You could park a car in the shadow of his ass.” ~ Geena Davis, in Thelma and Louise ~