I found that in general (I repeat in general, because I know every person is different and every situation is different), when a girl says to her SO "tell me the truth", she doesn't want the guy to either lie and say what she wants to hear, nor does she want him to tell *his* truth.
What she wants to hear is that his truth is the same as *her* truth. Because truth is a relative term, not an absolute one.
Hence the drama over questions like "do you think she's prettier than me?", about which guys often feel like there is no right answer.
She doesn't want him to think she is prettier, but then lie to her and say his girlfriend is prettier.
She doesn't want him to think she is prettier and say that he thinks she's prettier.
What she wants is that he thinks his girlfriend is prettier, and say that truthfully.
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I think most women who do that have low self-esteem which is why they're looking for a pick me up from their boyfriend. You're obviously right that they want their boyfriend to honestly think and say that she's prettier than the other girl. The problem with that is it becomes a loaded question due to her self-esteem. If he thinks the other girl is prettier and says so then that just makes her self-esteem problems worse and she gets hurt, but if he says that he thinks she's prettier than the other girl she doesn't believe him and accuses him of lying. It's a no win situation and I feel bad for guys who get put on the spot like that lol. Personally I think it's a stupid question anyway, (I think) every girl thinks there are girls who are prettier than she is so why wouldn't her boyfriend also think there are prettier girls out there too? It doesn't mean she's not still the most "attractive" one to him. Why poke the bear?1