“They’re all pretty, I guess, but I like you and [insert name of actress she likes] much better.”

“She’s definitely pretty. But you… you’re beautiful.”

Both, but I find (enter specific girl’s qualities) much more enjoyable.

I don’t put up with trap questions any more. If a woman is asking to have her ego stroked, I’ll either do it in a very obvious way, or I’ll just tell her what I think, and if she has insecurities, she’ll have to deal with them on her own.

You can not ask for a compliment, no matter how indirectly. You are still asking and that means you can’t get a real compliment. And if you do accept a compliment you asked for as real, then you have far more problems than I can help you with now.

Unless a compliment is given voluntarily, without having been asked for, it is worthless. I hate that game. Especially with women. If you are insecure because of what I might think about the looks of one of your friends, then we have much more serious problems than some little white lie can take care of.

Everyone has insecurities, especially women with society today. I think it’s an act of kindness that you’re thinking about her feelings.

Or maybe it was just a random question and she isn’t jealous at all.

Maybe you could channel your “inner Italian” and say that you think all women are beautiful, in their own way; but I don’t think you can pull that one off unless you really mean it.

@lillycoyote Oh, but I really do believe that.

@Imadethisupwithnoforethought If you really believe that, then you should be able to pull it off. So, maybe that’s your answer. A man who truly loves women; not a womanizer or just a flirt, but a man who truly loves women and thinks women are all wonderful in their own way… well, I at least, find that kind of man to be very charming and endearing; particularly one who loves all women but me, in particular. :-)

Mother Teresa

@Pied_Pfeffer Yes, she, Mother Teresa, was beautiful, in her own way, absolutely.

I wouldn’t think of answering such a question. Each is attractive in her own way. How do you define “pretty” as opposed to beautiful, cute, lovely, good-looking, and all the other synonyms for pretty? It’s a trap and you can’t win. Should you break up with her, I can just imagine her telling each woman your opinion.

I’m surprised so many of you automatically see this as a trap or an ego stroke question (though of course it can be). I’ve had this discussion with SOs and with male and female friends in the past, and it was just a part of learning about each other. In the same vein as talking about what books/foods/music/sports one likes. I find it pretty interesting how opinions of who or (what) is attractive vary from person to person… it just intrigues me. Long story short, I wouldn’t avoid answering it, but I wouldn’t be a jerk while I was answering it, either.

If it’s about what I think of our mutual friends then yes I would assume that the question arises out of jealousy and insecurity; worry that I might be more interested in one of them rather than in her. I would become suspicious that a woman so insecure is not the right sort of woman for me.

If we’re talking about celebrities it wouldn’t worry me as much – she’s not going to ever be concerned that I might actually run off with my celebrities of choice (provided she is of sound mind and not suffering from paranoid delusions).

Why not do the Jewish thing and answer her question with a question? Ask her who she thinks is pretty. Or, maybe ask her why she asks? It’s kind of an odd question in my mind. I know more or less who my husband thinks is pretty of my friends, who he thinks has great tits, and who he thinks is not attractive. So? But, not because I asked.

I never really have a discussion about other pretty women with exboyfriends or my husband, but certainly we both comment on beautiful people, especially women. I might say a woman is beautiful and he might also, but it usually is just a statement not a quiz.

First, is the woman you’re somewhat romantically linked to natural pretty or makeup pretty?

If your girl is makeup pretty rather than a natural beauty then pick one of the friends who you find least pretty of the makeup pretty and say you like the girls who take time on their appearance.

If your girl is natural pretty then pick the plainest of the natural looking friends and tell your girl you like the look of girls like her (your girl) who are natural looking.

Good luck to you!

@augustlan makes a great point. I ask my hubby all the time about who his current favorite actresses are. I listen to who he waxes poetic over, then I dress up like her and jump his bones. It’s fun. :D

One should also note that he always knows who I’ve got the hots for, and he doesn’t care. We’ve had previous conversations about the possibility of him wearing a hat and braiding his goatee, so I can scream, “Oh, Captain Jack!”

Two of these answers sum it up for me.
One is @wundayatta‘s refusal to answer ‘trap’ questions which is a wise way. It does a relationship no good at all catering to insecurities and gotchas.
Then there’s @WillWorkForChocolate where the answer is actually welcomed in a context of trust and no threat to the relationship. That can be big fun.