Cracking your homeboy is when both of you are absolutely chopped and pull absolutely zero bitches, so you resort to having sex with each other in a heterosexual way.
Mason: Do you want to go out with me
Girl: No, you’re ugly af
Mason: That’s ok, I’ll just crack my homeboy, Calvin
Girl: Really? Cracking your homeboy?
National Set Your Homeboy Up Day is on the 25th of May. Representing love and passion, all homegirls must set their homeboys up with one of their homegirls!
Yo bro today it’s National Set Your Homeboy Up Day!!! I can’t wait for my homegirls to set me up!!!