You bet your life
We had our first father-son tournament last year, while playing a late-season round at another club. There were no actual family pairs present, so we went by age: Nick and Gene (65 and 73 at the time) against Tim and me (both 51). We got the idea because Nick, when speaking to pretty waitresses or cart girls, will often refer to Gene as his father.
The fathers led all the way that day, but then the sons birdied three of the last four holes and won on the 18th green, 1 up. Tim and I reinvested our winnings in gas for Gene's van, which we think of as our off-season clubhouse, although it predates air bags and fuel injection, and it gets lousy mileage.
We tried the fathers-vs.-sons format two more times last year, with larger fields. The dividing line between the two generations was somewhat blurry: The oldest son was 58, the youngest father was 60, the youngest son was 40, and we don't know anybody older than Gene. The fathers won both times, by comfortable margins, and we've kept the format going this year, on days when we aren't busy playing something else. So far, neither generation has a preemptive advantage, partly because, on any particular day, whether you are a father or a son depends mostly on who else shows up.
It's fun to play games that last for more than one afternoon. A friend of mine has been playing a $5 nassau with the same guy almost every weekend for many years. They decided at the outset that they wouldn't pay up until one of them got more than $200 ahead; so far, no money has changed hands. My brother, John, and I have an unspoken competition whose purpose, from my point of view, is to see if I can beat him, straight up, for the first time ever. That competition has been going on for 16 years.
Late last year, my friend Tony and I decided to play a match that will last for the rest of our lives. We got the idea after tying an informal 18-hole match and then tying two consecutive 18-hole playoffs. The second took place on what turned out to be the last golf day of 2006, so we figured that we had finished that year all square. "Let's just keep going," Tony said. So that's what we're doing. The match resumes every time we play together, and the hole-by-hole scoring (recorded in an Excel spreadsheet) is cumulative. The winner will be whoever's up when the first guy dies. I'm eight years younger than Tony, but he's in better shape, so you never know. Besides, either one of us could get run over by a golf cart.