Things that are of value are double-edged swords. We can get immense happiness, joy and utility from having things that we value, but at the same time we are susceptible to the pain of not having those things we value. Additionally, we are also liable to experience the troublesomeness of having to strive for those things we value. For example, a woman who wants a man who is both competent and good looking certainly has more on her plate to deal with than one who would just rather have competence. But at the same time, having more things to value means that you're more selective, which means having higher standards. People chasing things they value are likely to enjoy the hunt itself and play it like a game.
Choosing to follow a philosophy of life that is more zen (where detachment means no loss and no unhappiness) or more liberal (where it is better to have loved and lost than not loved at all) might ultimately be a matter of what one tends to gain or lose.