It seems pretty dumb to try that game with her, but I suppose he's desperate to find at least one way she gets embarrassed.
If he wants to harden himself, just tell her to not hold back so much.
When it comes to liking things they do for you, and they do for themselves, people usually appreciate whichever is rarer more. If it's a good person. Some people will only appreciate whatever's done for them, and then usually not enough of it.
"I got to see you smile again, and..."
To be fair, it's an adorable smile.
Trying his best.