You could do that, but the likelyhood that you would get a straight answer wouldn't be very good. He'd probably tell you he thought you were attractive no matter what, as unless he was trying to be intentionally rude, he'd probably not tell you that he didn't think you were good looking (if that's what he really thought).
If you came up to me and started hitting on me and asked such a question, if I thought you were attractive, I'd tell you. If you were just asking matter-of-factly "hey, do you think I'm attractive, I just need to know and I'll be on my way, I'd just be honest if I thought you were average or beautiful, one way or another.
Going up to some random guy in person isn't going to merit you very good results for accuracy, as it is only one guy. Also, if he thinks you're flirting with him, he might not tell you he thinks you are only average if he wants a chance with you. What girl doesn't want to hear she's the most beautiful thing ever? The guy might lie out of self-interest.
If you really want an honest opinion, you should upload a picture here on GAG and turn this question off fro anonymous and post it with your actual image or a link to a image upload of yourself. You'll get far more guys to answer and a better and broader idea of what guys think of your looks.
I wouldn't think she was insecure. That's a very bad assumption to make based purely on someone's actions.
It WOULD be pretty weird, though... but in a good way. I like weird. Weird means they're not boring. ^^ Which also means it would be interesting.
Also, just like the insecure part, I wouldn't assume she was confident. I'd be more inclined to think she was simply curious, more than anything else. The fact that not a lot of girls would ask about this though, would make me curious too.
And yes, I would answer honestly. :o If she had the nerve to come up to me and ask about that, I would tell her just what I thought. :p And then maybe ask a few questions of my own, like what made her ask me this, etc. It would be fun. =D
I'd be very confused. I'm actually very shy so if I did think she was attractive I wouldn't be able to tell her that because I'd be too busy wandering why she was asking me in the first place. Did her boyfriend just dump her and I just happen to be there for someone to vent to, does she like me, should I tell her I like her, is she setting me up for some joke, will she laugh at me if I ask her out, can I ask her out? All of this and more would be going threw my head and because of it I tend to clam up and not be able to talk at all.
I didn't have my first girlfriend until I was 23 because of my shyness with girls. I think the girls who I did talk to thought I was gay but I was always to scared to ask them for advice because I thought they might get the wrong idea and think I was asking them. Especially one girl in particular who I was friends with in high school. I had a crush on her best friend but couldn't talk to either of them about it. I couldn't even talk to my friend whenever my crush was around her.
Anyway my first girlfriend asked me out and I said yes mostly because it took the pressure off from needing to talk to someone I liked. Problem was I never liked her that way. She's still a good friend but I just didn't have any emotional connection with her beyond that. After we broke up another girl I had been crushing on for 3 years asked me out. She was attracted to me and likes me as a friend but the relationship never really advanced on an emotional level for her and she broke up with me. That's my entire dating experience and I'm going to be 26 in 2 weeks.
It would be nice to actually be able to walk up to a girl, talk to her, and ask her out. It'd also be nice if most women didn't feel like it was the mans job to do all the asking. I don't know maybe I've already dated the only two girls who don't have this outdated idea that the man has to ask them out. I'm more talkative to girls online because I'm not distracted by how pretty they are but not doing very well with the whole online dating thing.
All this being said, if a girl does ask me about her appearance does that mean she's attracted to me. Some times female co-workers ask me this and it's even more awkward because they're all in high school and I don't know if I need to have the "I'm too old for you" talk or not.