"Wow, I am SO out of shape!"

SHE SAYS: "Wow, I am so out of shape! I need to get to the gym!"
YOU THINK: "Well...

a) "... yes, finally! Go lose some, puh-LEASE."
b) "... honey, I think you're perfect; here, have some more cake."
c) "... Jim?!? Jim who?! Woman, you cheatin' on me?!"
d) "...okay, me too; haven't been in ages."

This one is pretty obvious, but it is representative of a whole slew of statements from girls that ask, or seem to ask, to be contradicted. As a general rule, when a girl bemoans the future effects those éclairs will have, she probably isn't really thinking about what you are going to say, she is just thinking about the éclairs; unless she is really insecure, this isn't fishing for compliments. But, this is the sort of question that can lead to rather ticklish answers. If you think a) is an option, I applaud your honesty and hope I never meet you. Even telling her that she is hott stuff and that working out is sooo unnecessary probably wont get you a great response, because if she is honestly thinking her health, protestations of sexiness are not really all that relevant (though perhaps not unwelcome either). Don't tell her she needs it, or that she doesn't; that is up to her. Making it instead about you is generally a pretty good answer; although if that is your solution to everything than you run the risk of earning the Self-Absorbed-Prick title (beware). This is the kind of statement that should not be a big deal, so don't make it one.

Essentially, this is a good way to treat compliment-fishing of any form. When anyone, male or female, makes intentionally self-deprecating remarks to get attention, contradicting their bull shit won't help them OR you, and going along with it is, while occasionally tempting ("Wow! You've convinced me, you in the size-zero-jeans; you really ARE fat. Happy now?") is often less than kind. Girls usually say things like that because they are scared it's the truth and are desperate for assurances that it is not, but if they are asking you if you think they are fat, they have almost certainly asked someone else before, and your answer isn't going to convince them either, so don't bother strenuously contradicting their silliness. It doesn't hurt to be kind, however, and if someone is whining about exercise or their weight they probably just want a little support, so give it to them without belittling or insulting them. :)

"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.