Newly single Tyler Williams ought to be out partying every night, sampling the buffet of gay men Toronto has to offer. Carefree and casual has never been his style, even less so now that he's a tenure track history professor approaching thirty, but he has a better chance of finding Mr. Right in a club than on an app. Distraction from his dismal love life comes in the form of a housewarming gift - a life sized portrait of a gorgeous naked man, complete with a mystery. Maxwell Friedland, a Depression-era artist, went missing shortly after posing for the portrait, presumably murdered by his lover. Finding out more about Maxwell and his disappearance plays right into Tyler's love of both history and murder mysteries, but before long, Tyler finds himself obsessed with the man in the painting. It's not long before he starts treating Max like a silent companion and sounding board. Max doesn't judge or tell him he's a failure at dating or cheat on him. Everything he learns about Max makes him