There are instances when it is appropriate to think about winning or losing. That is in competitive games like soccer or baseball. There is a glory and a deep satisfaction to winning because you put a lot of hard work into it and you come out on top. This only happens with great respect for the opposite team, without which there would be no game and therefore no glorious win. When winning matters more than respecting the other players or the game itself that is when you have doping and cheating and the breakdown of the true spirit of the game.
In the world of business there are winners and there are losers. This “game” of business is a fair one as long as everyone has a fair shot. With the advent of high inequality, near monopoly, discrimination, and un-regulation, the big guys get bigger faster, and the small guys stay small or go out of business. Well balanced and well regulated economic conditions can allow for everyone who wants to be successful in business to do so.
There is no winning in true love. In romantic love, you may have one guy take the favor over another, but in true love there is no winners or losers. The reason why is because true love is grounded in the innate value and preciousness of all beings, which is equal in all beings, and therefore no one is put above someone else in true love. Even if people have done bad things, or if they are a saint, each one is at their own stage of growth and development, and each one is an equally precious heart. Think of it like this: can you say that one child over another wins at your love for them? Or that one would lose at your love? Any truly loving parent loves all of their children without favoritism or bias, not withholding love from one and exaggerating another's, making sure each one knows they are loved equally. Otherwise they would always be vying for the love of their parent and never be restful.
True happiness in a community comes from the mutuality of hearts, that they all come together as one. In this case, each one is just as precious and vital to the community as another, and no one is ultimately loved less or more because of who they are. There may be leaders and those who mostly follow, but the organism of the group is alive as a whole based on all the parts living in union, which is in mutual and equal love and respect.
It is natural to say that you love your family members more than you love your enemies. However, in multiple spiritual traditions it is taught to try to have deep love for everyone. In Buddhism it is a regular practice in loving-kindness to try and regard your family, strangers, and your enemies with equally deep love. In Christianity, Jesus taught, “For if ye love them which love you, what thank have ye? for sinners also love those that love them.” Thus, it is our opportunity to expand our hearts to be able to love everyone, no matter who they are or what they have done. May you come to know where winning has its place, and that in true love there is no winners or losers, only lovers.