I'm going to date someone my friend used to date.
Do you think your friend will mind if you date this person?
Yes, but I still want to hang out with them both and I don't want any problems.
I think it's okay for you to date whomever you'd like as long as everyone involved is fine with it. Just make sure to be honest with your friend and be sensitive to their feelings
I'm glad you think it's okay, I'm interested in dating their most recent ex as well.
Is there a reason for why you want to date many of your friend's exes? Maybe you should consider dating outside of your circle, as there are many fish in the sea! Things can get complicated when you start dating people who have relations to people you know.