Make suggestions, see if he picks up on it.

"You want to see that movie? Yeh me too. Are you going to see it next week when it's out?"

"You haven't played tennis because you can't find a partner, I have the same problem. Noone wants to play tennis anymore. Though I'm pretty busy this weekend, ask me next week and I just might help you out".

"So you are free on Sunday. What would you like to do on a Sunday? Hmm, are you a mind reader? I was thinking about doing that too..."

__________________
My Demon revokes any prayer
He's grown contempt for love and hope
He betrays trust, twists truth and fair
Indifference is his way to cope
Engulfing sound of sensations
He quells with voices of despair
And muse of short lived inspirations
Flees at the sight of his cold stare
~Moy Demon - Mihayeel Lermontov~