Does this dress make me look fat?

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!

See also:
"How do I look?"
"You're not going to wear THAT are you?"
"I don't have a thing to wear!"
Getting ready to go out
Shopping
Therapy

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."

What was the question?

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

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.

Does this dress make me look fat?

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

Where's my fork?!

Kudos to Dave.