Lyric discussion by Guitarearl 

Cover art for On The Lookout lyrics by Barenaked Ladies

I think Jim Creeggan may have the most underrated voice out there.

It's an analogy of the time when a couple realizes that they want to spend the rest of their lives together, compared with an adventure-type scenario. You get the impression he thinks of their single lives as boats, and they came together, sailed together, and eventually the wind (desire to look elsewhere) brought them to "the lookout." That's where they decide to "look out" towards their future and come together for good. The commitment they both realize they're making has them look back to see their pasts of being apart, lonely, etc, dashed by waves and wind. And from there, it just moves so fast through the stages of love.

The whole bit about the rockface makes me think of the years after one is married. Tough to hang on to what you have, but in the end he recommits to caring for her.