I would not send a picture. If it were for the boy to see, I would probably nix the shidduch. If the mother wanted to see it, I wouldn’t send it either (she is not the one who needs to find pleasing aesthetics), but I would still consider the shidduch if they were willing to go ahead without the picture. (I am b”H a real father, but the situation is hypothetical).
Now, golfer (and anyone else out there, real or hypothetical), what would you do if the mother wanted to meet the girl first?