Here is the correct response to this question:

  1. quickly GLANCE at the woman (Anything more than 3 seconds is too much time)
  2. say, "No, dear" and go back to reading your magazine/usenet group/everything node - before both words are entirely out of your mouth.
  3. if the woman follows up with "Are you sure?", don't even look back up, just say, "You look nice." If this does not keep you from getting in trouble with your girlfriend/wife... she needs therapy!

The only proper response to this complex question is "Honey, I love you." Nothing less, nothing more.

I think a good "safe" answer is to leer and say "Take it off, and I'll let you know, bayBAY!" Add lip-licking and slurping noise punctuation to taste. This response has the double virtue of
a) answering neither the question nor the implication.
b) inviting sex.

It does not get you off the hook; it may be interpreted as a complete disregard for her appearance concerns. At least it has some potential positive results.

In one of the Philly Phrolics seminars I attended, the speaker noted that your lady is probably asking, NOT to put you in a double bind, NOT for a pat of reassurance, but rather because she simply wants to look her best. Think about it: if you were about to make a fashion blunder, you'd want to know, right? So, assuming she does in fact look fat in the dress, the tactful way to indicate it is by suggesting something that looks better. "I like the blue dress better than that horizontal striped one." "I think the red number is much more appealing."

I'm sorry. I was distracted by the lovely circus tent in front of me.

What was the question?

In all seriousness, any woman who asks this question with any regularity needs something other than therapy.

For the nth time: Insecure women are no fun at all. Zip. Zero. Nada.

Wonder why men tense up and begin to tremble in fear when you approach with a dress and "Does this make me look..." on your lips? It's because we know that constant questions of this ilk are a sign that nothing we say will ever assuage your worries. Since most men thrive on successfully fixing problems, this presents us with an emotional black hole, with someone we love and care about at the center.

Please. If you want a quick opinion from us, ask. And then take our answer for what it's worth: the snap judgement of an article of clothing we will never wear and which inhibits our access to your naked form. We're not gonna give you the answer you want...because we don't know what that is; and even if we did, you wouldn't believe us.

Honestly, you don't really want our opinion. If you did, you'd have us pick out your clothes in the first place. We're happy as long as you're wearing something that is mostly clean, isn't see-through (except when we're at home...then the more transparent the better) and that allows us to leave the house in some semblance of a timely fashion.

We want you. The wrapper is incidental. I promise.

Why do you ask if you don't want a truthful answer? If you ask I'm not going to lie for you. If somebody asks something and you want me to lie to them, I'll consider it because you're not responsible for the question having been asked, but if you ask the question, you're responsible and have no right to demand I lie. Anyway, there's no point to lying if you know it's a lie. It's just stupid.

Inquire: To seek for truth or information by putting queries

That's what questions are for. Don't abuse them. If you ask, I'm going to answer truthfully.

This may be just me, but when I ask this question of my boyfriend, I actually want him to tell me whether the dress makes me look fat!
I have a certain body image in my mind, that unfortunately got stuck when I was around sixteen years old and several kilos lighter. Whenever I look into a fullsize mirror I am struck by how much I resemble my mother nowadays (this is not a good thing). Automatically any item of clothing that seemed fabulous on me in my mind's eye loses much of it's appeal in the harsh light of the store.
My mental body image also greatly varies with my mood. When I'd just found out my leather trousers didn't fit me anymore because I'd gained weight, I couldn't shop for at least a week because everything looked horrible on that horrendously fat body with the stupid way-too-short legs. When in love my body image is a lot better. Then I tend to buy clothes that are not really 'my thing', because when I feel great I think I look great in anything. (I don't. Trust me.)
Because of all this, when I try on something new, I need someone with me who has a more stable view of me and what suits me. Here's where the boyfriend comes in, and gets asked the horrid question: Does this make me look fat? If so, the dress goes. If not, the dress gets to be bought. There is no right answer, just a truthful one.
If however someone gave me the answer kslawson provides above, I would be sure the person in question found me VERY fat but just didn't want to admit it.
In one of Dave Barry's columns he declares that the only appropriate response to:
Does this dress make me look fat?
is for the questionee to stick a fork into one or both eyes. Much less painful than answering…

I have taken this to heart, and whenever my wife lets slip an unanswerable question I holler:

Where's my fork?!
She cracks up, I dodge a bullet, and innocent bystanders are spared potential unpleasantness.

Kudos to Dave.

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