Should I ask this boy to be my Valentine?

I feel that you should do whatever your heart desires. If you feel that you should take the plunge headfirst into this cold, dark pit of wonder, by all means, do just that. It may express your true, serious feelings for this fine fellow, and if, in a modern-day montage of romeo and juliet will unfold before the world's clear eyes. He may even have the same feelings for you, and what a cleansing effect that would have on your conscience.