I know you’re all wondering on what I have to say about Winnie. I shouldn’t reveal too much here as this is a big part of the story which you will learn in due time. Winnifred Trainor was set out to be one of the major tragic figures of the story, but she had her hand in the tragedy too. So let’s be clear. As I was not the mythic figure, she was not the tragic figure, either.
Winnie was 27 years old when I first met her in 1912. I was 34. At this age she was considered to be a spinster and at my age, I was a bachelor but the state of bachelorhood was much less called into question than spinsterhood. Men were expected to be free until such time they decided to settle down. This was not the case for women, and I believe this had a bearing on her parents’ view of her and of me.
To be sure, we had a grand time together. Each time going up North, I enjoyed her company as she was not like the other women. Practical (and mathematical she could tally a bill in her head with no paper and pencil), she had an equal love of the outdoors that she shared with me. We spent many pleasant hours together, fishing and canoeing. Her family came to know me well and had the (unstated) expectation that the relationship would become more formal one day.
Tom Thomson's Last Spring 