Written in 1985, "Worth Winning" by Dan Lewandowski is about a man who tries to win a bet that he can get 3 very different women to accept his marriage proposal. Some may find it a rollicking romp, but I just found it unpleasant. It took forever to get through.
I know it's fiction, but how often do people really make bets like this, which are also a staple of romantic comedy (e.g., "How to Lose a Guy in 10 Days")? Why do writers rely on implausible plots like crazy bets, people thrown together at work who just happen to be exes, the guy taking on one last job before retirement?