have an idea of what it is you want. i’ve been through similar conversations with some of my friends with situations like this. it’s much easier to talk to people and have a conversation if you know what *exactly* you want. communication is key here. be very transparent, and ask that of him too
potentially, it depends how muddled your feelings are. A good place to start is to ask yourself if you want to date or not. that usually sets the tone well enough, and is a good way to lead into other questions, such as “if we’re not dating, do we want to continue having sex?” “do we want to do this regularly?” etc