Nineteen years ago, when my wife and I were just barely acquainted and I was too shy to ask her out, we made a bet of a case of Corona beer about something a mutual friend would or wouldn't do. She won the bet and a few days later I received an anonymous envelope containing a promotional calendar with her business name on it. I flipped through it and found she had cut out little pictures of cases of Corona beer and pasted them in all of the days of the current month. It doesn't seem like much looking back, but we were both extremely shy, and her doing that was enough encouragement for me to ask her out. As they say, the rest is history.

That's the best bet I've ever made. I lost, but it's paid off every day since.