Mr Deplume just tagged 1/8 of a mile barefoot onto the end of his run. He's been in Nike Frees for a while, but I never thought he'd make the jump, even part-time.
I've never asked him to try it at all. However, I did suggest that he might be able to keep his long slow runs slower if he listened to audiobooks while out running (he kept running them too fast). First book available from my computer to his mp3 player: Born to Run.