Fyl. It really is tough for friends to go to that level if friendship has been established. Not impossible

Maybe he meant it literally?

It's not 21st century courting if you don't share nudes. If you send him ten, and he sends back ten, that's the sign for you to go Instagram official. Kim and Kanye did something similar, only she posted so many that thieves worked out where she was staying, and were able to rob her, and he kept getting angry whenever people asked if he liked fish dicks.