A former colleague told me he'd found a way to spring the trap. He called it the "like a whale" exception. He explained, his wife - who I think was with child at the time - had put on a sun dress and asked him the dread question and I guess he was feeling suicidal that day. "Like a whale," he said. There was a pregnant pause and then she burst out laughing - and never asked him that question again.
Excellent response. There are few questions the American male fears more than being asked by his woman, "Does this X make me look fat?" And with good reasons too given how touchy of a subject it is today. It would be illogical to say that most women care about their weight, however, since something like a 2,358,029,044% of the country is morbidly obese grotesquely overweight pleasantly plump. The key to answering a question like that is to be cocky/funny with it. Merely saying, "No, of course it doesn't" is a failed response because she is expecting you to say that. Responding with a "Yes" is also a failed response because there's nothing more attraction-killing than drab, dull honesty with not a touch of wit about it. So, responding with an off-the-cuff remark like, "like a whale" or something to that effect, said with a smirk, can get a girl to respond very positively to it. Why? It's not expected and it's obvious that you're joking; one of the reasons why sarcastic humor like that is funny is because it's over-the-top, it's ridiculous, and she knows it.
Now, obviously you don't say something like this if she's "extremely" sensitive about it to the point of having a complex, but for the 99% out there, err on the side of cocky/funny rather than forthright honesty (be it "yes" or "no"). Being cruel about it, even though she's average weight, by saying, "Yeah, you're disgusting, lay off the pork-grinds and pasta for a bit, will you, you slob!" will send her packing. Neither cruelty nor honesty are called for, wit is. How often does she hear "no, you're not fat, you're gorgeous!" and still she asks the same question? She's not looking for another "No", she's looking for somebody to crush that nagging question in her mind and the way to do that is with a smirking blast of sarcastic humor. The commenters to that article were overwhelmingly in favor of saying, "No, you're not fat", thus showing that they missed the point. Teasing a girl by making ridiculous statements about her weight, "Geez, I'm surprised they let you on the second floor", "Better stay out of the ocean, I hear there's whalers in these waters", etc will usually make her laugh, lightly punch in the arm and call you a jerk. Personal anecdote: I've never seen somebody lose a female friend by teasing her about her weight, it just makes them laugh.
Be cocky, be funny, loosen up and others will too. Confidence is like a disturbance in the Force: detectable even from great distances.
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