I thought it was very sweet and I had no idea that at some schools this is the norm or expected!
Here's my naivety again. Why would anyone be leery of this boy? All he did was sing for the girl?
I'm pretty sure it wouldn't be expected in our school but it wouldn't surprise me if someone involved in choir/drama did it. Now if it was someone who wasn't into singing and this all of a sudden happened in math or science class....THAT would be highly unusual.
Then again, I have my DD who said in front of her boyfriend that doesn't even go to our school that she was going to Prom with or without a date next year.

It's perfectly acceptable to go to dances solo here. I almost think it's unusual to actually have a date for homecoming - things have changed a lot since I was in school -- they give you free with purchase items with homecoming tickets, last year it was a small backpack bag, this year an ID holder


I'm always amused by it, seems almost like they are bribing the kids to make sure they buy homecoming tickets. No other dance gives away "free with ticket purchase" items here.
I have no idea why someone would be leery unless they thought the boy was moving too fast with going all out for Prom?? Of course, we don't know if they just met this year or have been dating since Freshman year (or before). If they say just met last week or something OR weren't even dating, that might make you take a step back and go, whoa wait a minute, that's a bit much, otherwise, I don't see an issue with it.