This is a beautiful, but melancholy, song. The singer is thinking about a lost or separated love. Here is a live recording of Sylvia Hotel that you can find on YouTube.

Cheryl wrote this song shortly after her breakup while staying at the Sylvia Hotel in Vancouver, British Columbia, which looks out over English Bay. She had finished her show and went down to the bar for a drink, feeling sad and lonely. It was raining and she was looking out the window and watching the bay. She reached into her pocket and came across a book of matches from The Durango Hotel. This is the hotel where she had recently stayed visiting "her ex". (Cheryl advises not visiting your ex after a breakup. It doesn't help) That was a joke :^)

One part that always gets to me is:

I don't wonder why you left

I wonder why you stayed so long.

This hotel must be quite something. It turns out that Bruce Cockburn also wrote a portion of "Wondering Where the Lions Are" at the same hotel. (Cheryl & I are both fans of Bruce.)