Oooh. I liked this, a lot. *laughs* Especially the ending; that puts the icing on the cake. Haha.
I usually don't like stories like these, but I did like this one because of the other things you tied into it, like the bikes. And I had to smile at the Cheshire cat reference. Very nice job!
Oh, this is pure delight (...and I usually hate smarmy Marauder tales.)
I especially like these images:
He would ask her out time after time, and she would turn him down. Sometimes the question would just pop up out of nowhere, and sometimes he would work up this big scene to catch her full attention.
Her mind screamed “NO!” by default, but her heart took a slow, burning dip into her stomach at the mere thought of him.
And the ending is perfect: shows an impish side to the rather staid Head Girl.