Guys, when would you try to guess a girl's bra size?

frankieisagirlname
Lol this happened to my friend. The guy she liked guessed her bra size and he got it right. 36C. I must say that is impressive that he knew. And when she got bigger he tried to guess again and it became an ongoing game between them

"38C?"

"No"

"36D?"

"No"

And etc. I'm not over analyzing I'm just bored and was wondering, guys why would you guess one of your friends bra size? just to about her? haha
Guys, when would you try to guess a girl's bra size?
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