Responses
I get it ( ̄∇ ̄"). So, two things: at this point, Ian doesn't trust Michele's sincerity and still feels the need to carry out these manipulative “tests” because of his traumatic past. Secondly, a bit of a spoiler, but there are certain truths Michele will never know because Ian believes keeping them from him is the best way to protect him.

HE COULD'VE JUST TOLD ANATOLD ABOUT HIS DAD BEING A PEDO DOUCHEBAG, BECAUSE HE KNOWS NOTHING ABOUT HIS FAMILY OTHER THAN SURFACE KNOWLEDGE ABOUT THEM AND WHAT THEY'VE BEEN SHOWING HIM, PLEASE STOP PLAYING WITH HIM, HE'S INNOCENT (/TДT)/