Milk Shoe

When an ugly guy that isn't very funny, nice, or interesting dates a much more attractive girl with a better personality than him.

Joe DiMaggio and Marilyn Monroe, that relationship was the greatest milk shoe of all time

Guacamole feet

Used to describe someone who is sad or depressed. Often a downer or party-pooper.

Tim, you just shot the birthday girl. Why’d u do that?
I don’t wanna talk about it. I have guacamole feet.