Why do I always think when I get a girl to like me it was a fluke or I got lucky

[Superus]

I don't know if this is a self esteem issue but everytime I peruse a girl that I find really attractive and I finally get her..I think that I got lucky? I try to tell myself I'm attractive and I even hear it from the girl I pursued.. But I always have doubt in my mind. all her friends think I'm cute/hot but I just don't believe I am? This is soo weird.. I thought by going out with the most attractive girl in my school would make me feel attractive and boost my confidence but it's not and I'm not satisfied until I keep repeating my success. ahh I feel like I'm rambling but does anyone feel like this?

[EssexMan]

Yup. I don't think it's uncommon at all. I'm way older than you (I presume, if you're still in school) and I still feel that way a lot of the time. I think you gotta just try to keep telling yourself that your history (like going out with cutest girl in school) proves you are attractive.