I would ask why he doesn't make money off his fame. He could sell videos or artifacts of fail to trolls. He could also have private interviews online and charge people. It could be the most money one could make in private chat and keep their clothes on. (I hope! I seriously hope!) If I woke up one morning and magically became Chris, I would make as much money as I could until the world gets sick of me.
"How would you like to make big piles of money off Sonichu without having to produce any new content or interact with anyone except me, and I promise I'll stoically endure your bullshit?"
Then I would make a Chris-Chan website with ads and self-publish every issue of Sonichu and become a THOUSANDAIRE! Plus I'd have him charge $50 to autograph an issue and $100 for a personalized sketch (Note: Sonichu Inc makes no promises regarding the content, style or effort put into the personalized sketches. Personalized sketches cannot be personalized and may or may not be sketches. If itching occurs after direct contact with the sketch consult your doctor.)
I'd ask this too. Although I think at first he'd just answer "well I plan to have a sweetheart by then".
And if you pressed the issue and showed how unlikely a sweetheart is for him, and asked what if he didn't have one by then, he'd probably get all mopey and say "well then I'd just DIE." in an obvious pity-fishing attempt.
I don't think he'd respond positively to that because he sees his life's troubles as the troll conspiracy. Never mind the fact that his life's problems are his own damned fault.