Madison Square Garden Night 2 and the mysterious person in the VIP box..
So... I decided to do some research what the exact position was of the VIP box

And I came to the conclusion that the VIP box was located at the right of MS. On this map you can see MS and B stage.The red arrows are the positions to face the crowd.The blue arrows are how to face the VIP box.On MS he needs to look at his right,on BS he needs to look left

Watch the location of the mixing tables. The are in his back when he’s standing on B stage

So let’s look at his performances of that night:
If I could fly - B stage - looking up at his left

Sweet creature - B stage - Looking up at his left

Medicine - Mainstage - Looking up (and pointing) at his right

Again Medicine - Mainstage - Looking up at his right

Still the one - Mainstage - Looking up at his right

Also Still the one - Mainstage - Looking up at his right multiple times

So I think we can state that the person in that VIP box is pretty important to him. During emotional, meaningful songs.. he keeps watching that box. While he was dating C at that time and she was standing in the crowd.. make your conclusions people..