What's the earliest you remember having feelings for a 2d girl? Before I ever got into anime, I remember having a crush on Phoebe from Hey Arnold!. I still love nerdy Asian girls with glasses, so some things don't change easily!
(Knowing her personality helps it make more sense)
The first crush I remember having from an anime was Sakaki-san. Still one of the best girls ever.
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jumin han from mystic messenger! i only played for a little bit because i hated yoosung (you have to get through his route in order to get to jumin's or pay money) so much i ragequit. i loved him because he had amazing gap moe and he made me laugh a lot. i miss mystic messenger!! i used to stay up all night watching comic dubs waiting for the next text messages. i also bought cat ear headphones to listen to their phone calls but they broke the day after i got them
Ty Lee from Avatar and Starfire from Teen Titans were the very first ones that roused some feeling in me. I've had an affliction for animated tummy ever since seeing these two when I was a youngin.
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As far as anime goes, I liked Asuka quite a bit from when I first saw Evangelion as a teenager. The first anime girl I was truly crazy about and would've called waifu material though was Chiaki from Danganronpa 2, who I still love and rate highly but not as high as I did back then.