In my headcanon, Clint got the Black Widow assignment and did what he always did--prepare slowly and meticulously and studied all the available info before going after his mark. So he got a hold of her file. And studied it. And studied it some more. In fact, I'd go so far as to say he damn near became obsessed long before he ever physically laid eyes on her. (And to my mind, that's when he started to fall for her--all that careful, obsessive attention to detail started to blur the edges between the personal and the professional.) He probably never even realized it at the time, but it played a big part in setting him up to make a different call.

And now I want fic about that.