To me it makes perfect sense.
Yes, of course Jose could have said 'No you are not going I want you here', but I think its a case of Jose wanting the lad to show him that he is serious about staying, not just saying he does! There comes a time in everyone's life when you have to make your own crucial decisions, no one can make them for you, its make or break etc.
Yes of course, we can all understand why the lad wants to go, so he can get a game each week, so if that's what he wants Jose is saying OK kid go for it, but don't expect me to take your ambitions at this club seriously. If you feel going on loan will develop your game, then go for it!
How the lad plays out this situation could well determine his future at OT, repeatedly in his presser today Jose refers to 'his, its the lads decision'.
I'm sure Jose thinks the lad can make it, that's why he brought him back after a year on loan, but does the kid really think Jose is going down on his knees and saying "Oh please, please don't go..." for me this is Jose giving the lad a chance to show he is maturing in his attitude, which has been the big draw back, in the past, his skill is not I feel in question.