Depressed WAW, digging in, learning about myself

[MrBond]

Maybe I'm confused. You WANT her to go out with someone else?

"We then had a brief conversation about how to pick up clues"

So you were encouraging her to date other guys with coaching?

"Is she now going to be more open to the possibility of someone else?"

Why not? Isn't that what you just encouraged her to do?