Pepper/ Phil
And Tony probably shouldn't have slept with his assistant, but there had always been that tension there between us as well. I'm not sure I would call it a healthy relationship either, at least not in the beginning. He was codependent and I enabled him to make terrible decisions, but it worked out.
Maybe it can work out for you and May too. It sounds like you need each other right now and I don't see anything wrong with that. SHIELD doesn't exist here, Phil. If ever there was a chance for the two of you, I'd say this was it.