to "play for bossie" means to bat for the other team, be on the other bus, butter bread on the wrong side. "to play for bossie" means to be homosexual.
eg. "that ogre plays for bossie"
eg. "he used to play for bossie but now he likes girls"
A play date is basically when you hook up with someone without fucking. Doing things like making out and watching Netflix just for fun and then never talking about it again.
Chad: “Bro did you guys hook up?”
Ryan: “No, it was just a play date.”