Start by sketching the basic shape of the girl's head and face. Then, focus on the eyes to show the sadness and the tears. Add some frown lines and a downturned mouth to enhance the expression.
The girl might have a crying cartoon face because she's feeling lonely or had a fight with a friend. Or perhaps she saw something that really touched her emotions in a negative way.
The big woman's baby in the cartoon might be crying because it's not feeling well or because it lost its favorite toy. There are many possible reasons.
It could be for comedic or satirical purposes, making light of a particular situation involving the player. Or perhaps it's a way to humanize the player and show their vulnerability after a challenging game.