I kinda want a story with her middle school look, but since they've already progressed this far...
How about a story of their daughter who looks exactly like her back then?
I like that description. Her smile certainly does make reading this very worthwhile, and of course so does the sweet Vanilla present.
The love of an old classmate who was happy you were kind to her...Yup, I mean, our protagonist seems like a decent enough guy, so I'd say he deserves it.
Great ending though! She certainly has a way with words, as I'm sure our protagonist can agree.
How about a story of their daughter who looks exactly like her back then?