We rode up the "big, high-traffic hill" tonight to eat dinner (maybe 6 mi. RT). This was a pretty big breakthrough for my wife, as it's the farthest away she's been on a utility trip. As we were eating, the bottom dropped out of the clouds. The waiter made a comment about how he hoped we parked close. I laughed and held up my daughter's helmet. He gave a nervous smile and left without saying a word.
As fate would have it, the rain stopped as we finished our meal and we had a pleasant ride home.
My wife made several indirect comments after we got back to show that she's now considering this ride to be practical and started brainstorming other places she could get to on the bike.
I'm pretty happy because I've been trying to sell her on either a) an in-town move to a place where we could both bike to everything we'd ever need or b) a move to somewhere like Portland/etc. The more often I can get her on the bike or bus, the greater my chances are.