I think she's trying to see if you check out her friends, and yeah it could be an insecurity/self-esteem issue. I think it is stupid (even though I have asked that question but not about a friend) because I wanted to see if he had the nerve to say it and to let him know that I was upset but in the end we only end up even more upset. My teacher said that girls always do this, and to prevent from happening a guy should just be honest and say "yes. " He said this would make a girl stop asking those questions and honestly I think it's true but it is messed up to hear it.
I don't think it has a lot insecurity but maybe fidelity! If you pick someone other than her- annnnt wrong. (Oh so you do want someone else) Someone prettier/better looking than her- annnnt wrong. (Whats she have that I don't) Someone not as attractive/good looking as her- annnnt wrong. (What is wrong with YOU). The best answer would be "huh" or keep repeating what she said like the question went right past yo, if you're lucky she'll get annoyed and change the subject. That's kinda along the lines of the am I fat question. ANY answer is a danger zone, either for you or her self-esteem so avoid it.
Yes she is insecure/low self-esteem. You don't just ask stuff like that even if she was trying to c if you were feeling here friend I don't think she would have wanted to know the answer because that starting nothing but trouble unless that's whats she's looking for. Never Ever if your girl friend is fine as hell never say she look better never comment on her looks never.
Wow for her to ask those direct questions, she is asking for trouble. Very much so, those are insecurity questions. Why would anyone want to know what friend her boyfriend thinks is hot. Be careful on answering those questions there. You are set up for TROUBLE!
It's most definitely an insecurity thing. If she was happy with her own image, she would realize that if her boyfriend really was more attracted to her friends, he would have chosen one of them over her.
You're f*cked! Just kidding... That is how girls are: they put you to test all the time. By the way, there's only ONE correct answer to those kind of questions: "None of your friends are as pretty as you, honey. So why should I care?" I hope you said something along those lines... otherwise you're f*cked! (figuratively speaking, sadly)
Nothing more than a curiosity question. Or it could be a test to see your reaction.