Women ask other women this dread question, too, and can act just as pouty and manipulative when answered. The question isn’t whether it makes you look fat but whether it’s flattering. I am very stern with my girlfriends who ask this of me, so I can see why a dude would hate the question, but it’s not that hard to handle. I tell her that if she doesn’t want an honest answer than she needs to tell me or I will give her the truth with both barrels. The gals who can survive my bluntness appreciate that I’m always straight with them.

My boyfriend has asked me the question, too, and I answered him straight. I think he was seeking reassurance that I still find him sexy even though he’s gained weight. I demonstrate how much I love and desire him nonverbally instead.

As a perpetually underweight man, I, too, have always noted that being an overweight man is not necessarilly a disadvantage with the ladies. I do not, however, feel that this is indicative of either a greater tollerance on behalf of females or a lesser one from males. I believe it has much more to do with the traditional and instictive roles of males and females as protector and protected. A large man is better suited to protect, therefore lending size itself a degree of attractiveness. Likewise, a smaller female looks more likely to require protection, heightening the masculine response.

Specific to the dreaded question, I think it often is just serving the purpose that many women’s questions do: to initiate communication. I learned a long time ago that men and women often ask questions for entirely different reasons. More often than not, when a man asks a question he wants specific information. When a woman, however, asks “what should I wear today,” she usually isn’t looking for a checklist of clothing items. She is, rather, trying to initiate dialog that opens communication and furthers the relationship. I know it is a gross generalization, but I have found that men are more likely to just want an answer to a question while women often want to discuss the question, sometimes not even seeming to care about the answer.

It pulls the rug right out from under their feet.

I always say, “No honey. It doesn’t, dammit. Here, have a slice of pizza…”

To which the woman’s usual response is, “You’re just saying that to make me feel better.” Come on, you’re talking to people who get put through the “no-win question” every day. The idea is to use ANY response as an excuse to throw a temper tantrum, not to actually get a sympathetic reply.

strcpy, you might want to be evaluated for Asperger Syndrome. I’m just sayin

Also, like Jaime, I see myself as thinner than I am (because I used to be way thin), then when I see myself in a photo or in a shop window, I’m startled by the fatty fat fatso.

Fortunately for me, I have a slight case of Asperger’s myself (making me half-Asped) so I have no concept of how I’m perceived and don’t much care.

But women really ought to stop asking those kinds of questions.

“How do I look?” permits him to say, “Great!”

The only time you should ask a man whether you look good in a particular item of clothing is if you’re deciding whether to buy it.

Also?

Women should stop dragging men along when they go clothes shopping. Don’t treat your man like a girlfriend with a deep voice.