It's the summer of 1952, and Lois is missing the love of her life. Her boyfriend, Bill, has gone to the Northern Ontario town of Kirkland Lake for work, leaving 17-year-old Lois, a Bell Telephone switchboard operator, back in Toronto where she pines for him daily. What else to do but write?
From July to September of that year, and again briefly in 1953, Lois wrote Bill at least 37 letters, which were found by her daughters after her death in 2021. Bill, who had died the year before, had saved them all for 66 years, lovingly folded into their original envelopes, and carefully stashed at the back of a dresser drawer. Interspersed with the letters are explanations, reflections, photographs, and historical notes on a time period rapidly disappearing from living memory. Dear Bill offers a glimpse into the pop culture and lifestyle of early-fifties Toronto through the eyes of a heartsick teenage girl, as Lois professes her love with unabashed candour.

In that post-war time period, some women, many of whom had joined the work force, were questioning the ritual of marriage and the role of wife. Not Lois. For her, it was simple, and she wasn't going to let up until she had that ring on her finger.