I KNOW! Only - and this is going to sound stupid - I can't quite figure out who with. Jo doesn't feel right, nor Ellen; I kind of feel it needs to be someone only tangentially related to hunting, because I can't see anyone in that community trusting an angel much farther than they could throw them*, and would probably be squicked by having sex with something supernatural/wearing a meatsuit, depending. (Sam notwithstanding.) My first thought was Cassie, actually... And I am tempted to write her. Very tempted. And it will not be all about Dean. (Ha!)

*Dean literally got dragged out of Hell by his, and said angel is still on probation.