Even when he could win though, he still gives it to his wife and daughter. That's thrown his win/loss ratio a lot over the years.
But minor things like that, guys do it all the time. Like buying two bags of cookies to share one when you know she'll 'secretly' eat the other in her office while you're at work. You just give your loved ones their little victory, there's no pain or loss for you in it anyways - just their happiness.