*heart breaks and mends all at once* probably the first time anyone has ever taken his metal hand affectionately <<< This gif is all I want in the world. I don't care that it's fake. I can die in peace. Someone has held TWS's left hand.
She does know from experience. He trained her in the Red Room. He doesn't remember her, and we've seen no evidence in the MCU that she remembers him from the Red Room, but these two DO know each other.