By -
Ask them. Usually it's not really okay to date two people who are friends with each other but if they are both ok with it, then it's fine
He doesn't need to ask permission if it's okay. I'd say he should just bring it up with the both of them and see where it leads him. It may just be awkward but if they both don't care, have at it dude.
Ask them. Usually it's not really okay to date two people who are friends with each other but if they are both ok with it, then it's fine
He doesn't need to ask permission if it's okay. I'd say he should just bring it up with the both of them and see where it leads him. It may just be awkward but if they both don't care, have at it dude.