Toe pain

This one's not for me - but for my bf, who's limping about moaning and groaning. He has a pain in his big toe which started after football last night. The toenail has gone black and is about to fall off (his other big toenail fell off last week - also football / running related, but less painful), and he's getting pains down the bone (close to the big toe). We managed a 4 mile run this morning, but not sure how he's going to fare on our 8 miler tomorrow.

What do people think - do you think the pain is related to his toenail falling off and will heel quite quickly? Or does it sound like something that needs plenty of rest? Or perhaps he needs a new pair of trainers...  Probaly we need to wait and see...! 

Lots of my toe nails have fallen off in the past... Once you pass the original stage of "the turn", which is where my whole foot feels incredibly painful. But then after that I've never really experienced any pain from it.

They start going black when any of my shoes/trainers/football boots have been slightly too small for me.