My best friend asked me if she is ugly. How should I have answered? (long)

I don’t think she was feeling me out for attractiveness. I won’t say why: just that it doesn’t fit the rest of her character.

In answer to some remarks upthread, I don’t really feel comfortable describing her in detail, but she is far enough from attractive enough that I think it quite unlikely she’d find another man. I think I’ll leave it at that.

First of all I would like to agree with the others that I got the sense she was feeling you out, to see if there was more than friendship there. Not just the question, but the lead up, “you are so attractive to women, my marriage is going well, do you think I am attractive…?” Just seems that way to me, but I wasn’t there, right?

Secondly, to argue a fine point, I have a few good friends that are LDR nurses and I asked them about ugly babies. You know they exist so I asked how they handle it when there is an ugly baby. They replied that you can always pick a feature, everyone has a good feature. Your friend knows that she isn’t particularly attractive to men, but maybe she has a beautiful smile, or killer lashes, you can always mention those.

Lastly, I have noticed it doesn’t matter how unattractive a woman is, she can always get another man. Whether or not he is a quality man is another story.

I would have either given her a look and said, facetiously, “yes. you’re a horrible monster and I can’t stand the sight of you. go away before I vomit.”

or said, “are you seriously asking me that?”

and then, when she pressed, just give a total cop-out answer like, “don’t ask me something like that. I’m really not a good judge. I would think you were beautiful if you had six heads, just because you’re my best friend.”

And if she pressed further, I’d point out her nice features and also point out features that she could improve on- like tell her she’d look really nice with makeup or she’d look great with red hair or, depending on how much of an issue to her weight is, that she might look nice if she lost a few pounds. This is probably easier for me because I’m a girl, but I’d do something like offer to make it fun- like when my friends complain to me that they’re fat and they are and I know exactly why, I’ll do something like suggest that we go to the grocery store and get some healthy foods and then go back to their place and cook a healthy meal, or I’ll suggest that we start going to the gym together.

My 2 cents:

She was looking for some emotional support for the time when she realizes that the object of her desires (the pesons she’s lusting after) doesn’t reciprocate. Then she can deal with it emotionally because her best friend affirmed that she isn’t attractive.

It’s the old deal of the human psyche making sure that they tie up the loose ends. It makes it easier to move on.

As for physical attraction, I once had an acquaintance who was one of the most perfect physical specimens that has ever been created. We were sitting a a bar talking. She was wearing a skirt that exposed her knees. There were scars on her knees. She told me that she had grown too fast and some surgical procedure had been done (I really don’t understand what she was saying, she was too beautiful to pay that much attention). I guess it was because those scars were the only feature she had that wasn’t perfect that those scars were a total turn-on. I can’t explain it but then, who can really explain the human mind.

Anyway, she put you in a no-win situation. Try not to explain yourself, dwell on it or let it affect your relationship. Move on like you were never asked the question. Don’t bring it up. She probably regrets having asked it so don’t even act awkward about it. You know the old saying about “Don’t ask a question for which you don’t know the answer.” That’s probably what it’s all about.

How’d she hook up with her current husband, then? Was it an arranged marriage?

Maybe he’s no looker? Sounds harsh, but something I’ve noticed is that attractive people, even if they aren’t shallow, tend to pair off with equally attractive people. A guy can be the best guy in the world, but if he’s handsome, he’s more likely to have his arm wrapped around a pretty girl than an ugly one.

She gave you an easy question.
Q: “Am I ugly?”
A: “No.” and leave it at that.

Very few people are truly ugly.

Incubus: Maybe, but the point is, that pot already found a lid.

There’s just no way I would give a proper answer to a question like this one; I’d probably exclaim “Awwww, now what the fuck kind of question is that?”.

First, I have to say, SurrenderDorothy, you’re good! You came up with a sequence of some pretty nifty evasive maneuvers there. You can be my best friend anytime.

But back to the OP’s question. I tend to have a pretty firm no-BS policy (partly because I prize honesty, and partly because I suck at comfort lying), so I would have had a hard time with the pick-her-best-feature-and-milk-it route. Instead, I probably would have opted for a tactic that a few other posters sort of suggested: I would have selected her *worst * (fixable) flaw and told her to work on it. At least I would feel like I was being constructive. Cold-hearted bastards like me like to hope we’re being constructive when we can’t manage being sympathetic.

That’s only in court: in everyday life it’s “Don’t ask a question unless you want to know the answer.”

You and Surrender Dorothy nailed it. I believe in honesty with friends, too, but in this case the honesty would have been, “That’s a stupid question to ask me.” Just reject it out of hand, but with a “you’re so silly” tone/smile.

IME, those kinds of questions tend to be almost blurted out. Someone has a deep insecurity about something, the general topic comes up with someone they trust, and bam: awkward question. No one with an ounce of self-esteem would seriously, deliberately ask such a question or put a friend in such a position, so laughing it off as a ridiculous question usually defuses the situation.

The proper response for a best friend when asked a question like that is “You’ve obviously got something on your mind – let’s talk about it.”

I’m guessing the real problem is her feelings about her marriage causing her to want to start an affair. That’s what she really needs to talk about! Instead, she left still confused about her marriage and the potential affair and now she thinks that you consider her to be ugly.

Your best bet now would be to get a hold of her, apologize for being dense, and tell her that she obviously had something she wanted to talk about but didn’t know how to bring it up.

Wondering how not to tell your best friend she is ugly isn’t what you should be worrying about when her marriage is on the rocks.