You have a friend? My boy, you have a GIRLfriend in waiting.
"not a couple
yet"
"
yet"
AAAAAAAA
But at least he knows what direction he's supposed to go, he actually wants to say yes and he actually tried to set a concrete date for a confession. My boy is trying to do things his own way, at his own pace. But that might've backfired on him if Umi really isn't available on Xmas Eve.
Just confess already! Learn from Umi, she can casually drop a love confession bomb without setting formal dates or anything.
Shouldn't keep her waiting for too long, might be rude even, because it doesn't quite honor the resolve she did to tell him she loves him.