chrunchyroll posted a poll result for the same question to both men and women
so i thought it would be fun to share my own opinion on something silly like this.
it's not going to be numbered though just who i think it would be fun to get chocolates from and why... maybe even how i think they would do it.
so in no particular order.
Kuroko Tetsuya - Kuroko no Basket.
you would just be walking along and then sudenly there is chocolate in your hand and a note with something along the lines of "will you be my light?" and yeah... would be adorable.
Kyon - Haruhi Suzumiya Series.
i know in japan it's mostly girls giving chocolates but being that i am a girl and i live in a country where it's kinda a mutual giving thing... most of this list is male
anyways Kyon would probably have to go through hell, alternate time lines and al that jazz and haruhi wouldn't know a thing... all she'd see was a simple chocolate and that would make me happy.
also for fun if she gave him a chocolate... bet she'd be wearing a ponytail
Onodara - Yowapeda
It would probably some extremly obscure random and rare toy or chocolate but he would just be so happy and saying something along the lines of "i biked as fast as i could to akihabara and it was the last one" and it may not be something you enjoy but you can tell theres a sweetness to it all.
Takashi Natsume - Natsume's book of friends
i could see him being really shy and embarraed about giving someone a chocolate (i actually hope he never gets a love intrest in the show cause i think it would get in the way... if it were taki i could tolerate it but still... no....) but yeah his chocolate probably wouldn't taste too good (since i can't think of a single instance where he cooks) but again at least he tried.
Seiji Matoba - Natsume's book of friends
he's shoot an arrown a hairs distance from your face and while smiling he would apologize since his depth perception is no good.... and knowing him he'd probably do it through your window just to add the creepyness of 'hey this creepy guy with a blindfold also happens to know where you live despite never having gotten your name.... and this happens in the manga so yeah.... i can see it happening.
Shuichi Natori - Natsume's book of friends.
he would just give chocolates to himself and practice his sparkle effect in he mirror. also he probably would send small store bought chocolates to every girl he knows with some non-descript message like "you will always be special to me" that shows n0 commitment but makes people think he's a nice guy.
i was going to come up with more but now it's the day and yeah... hope you have a happy valentines day... however you spend it
Edit: i thougth of another one.
Adol Christian - Ys
he would kick ass, take names, potentially destroy the god/devil/diety equivelant and make it so magic can no longer be used all to give you a simple chocolate.
Dogi - Ys
he would burst through a wall...