"Does this make me look fat?"

TRAP QUESTION. (No shit, Sherlock.) But really, as the fellow who suggested it for the title can attest, there is no good way out of this one. Ladies, you are a fool for asking (but, as a lady, who has asked, I understand) and gents... I am so sorry.

• SHE SAYS: "I'm not sure about this one. Does it make me look fat?" (or some variation thereof.)
• HE SAYS: ...

Dear sirs, herein lies the difficulty. Obviously, you cannot say yes. But alas, saying no often brings down the wrath of "you-lie-it's-dreadful" upon your well-intentioned head. The trick is that while no girl wants you to tell her the bald-faced truth (example: "your love handles rival the state of Texas for size in those jeans,") neither does she want to feel that you are being untrue. Therefore, the answer is to find a true way of telling her what you honestly believe (that she is beautiful) while still making some comment on her article of clothing (which she probably, but not certainly, wants).

So, when she says, "I'm not sure about this one. Does it make me look fat?" what she most likely means is, ...

• "I want you to tell me I am beautiful." 

or,

•  "I really don't care what you say and am going to buy what I want anyway but so help you god you better not say yes..."

or, perhaps she means,

• "I honestly don't know which one I prefer. Some advice please?"

As a girl who tries to avoid self-esteem issues and ways to make men cringe (as a general rule.. there are, of course, exceptions) I like to imagine that everyone who asks this question means the latter. (False, by the way.) Considering the former possibilities, however, it is usually safe to say that she looks gorgeous (if she ignores you, oh well, you knew what you were getting into when you went shopping with her anyway). The thing is, if I were trying on a dress and asking whether a guy thinks it's sexy... it generally means that I want him to say yes. Even if it's not a great outfit/dress/look, telling your gal she looks hot will probably be a positive. But assuming she really wants your opinion, please don't tell her you think it looks bad, or even less than great; give her your preference instead or make a comparison ("It's nice; but I really liked the red one") and throw in how awesome she looks. Just for good measure.