Well I don't think he's playing into it tbh.
He said that even if he loses he won't listen to the punishment cause he never agreed, but doing so would cause douchebag to flip out.
So the logical decision (Especiallysince he has a chance being 10th) is to beat him and call it quits.
To me anyways
My vote is for wingwoman.
Her reaction to the 2 of them in the room didn't seem like a jealous possible lover.
Like she didn't stay to see what was happening she closed the door and ran away to give them privacy, seems to me like it's leaning another direction with her.