The fact that he goes out of his way to talk about a very special iPad leads me down the path that maybe he's signed in to your iCloud account? If so, he's watching iMessages and any activity to contacts/calendars/reminders/etc...
A few clarifications that might better help us:
1. Is there some sort of bet or challenge?
2. Were you intentionally hiding?
3. Has your friend had recent physical access to any of your devices?
Boy have I hit rock bottom responding to this...fucking insomnia :(
1. after the comment was made and I questioned it, it then turned into a challenge. 2. Yes, I was intentionally hiding, so thought anyway. 3. No, He is 15+ miles away from me and to my knowledge he doesn't know my address, though that information is easy to find.
So is he yanking my chain, and the timing of his message and me getting on Facebook was purely coincidental and just perfect timing? Or was there actually away for him to know that I was online???