After giving it some though I arrive at a conclusion that picking a different breaking point for your line when it creates a list/bold ambiguity is a much simlier and easier to exmplain technique than any escaping. And since the newlines are ignored anyways, it doesn't constrain the possible output.

- Doctor, it hurts me when I do //like this//.\\
- Well, then don't do //like this//.

-- [[Radomir Dopieralski]], 2007-Mar-11