*You can only "win" against someone when you're judging them based on things they have control over. Their hair, their clothes, their makeup, the way they are acting, or some other embarrassing self-"controled" quality the may be exhibiting are all worthy of a "win".
Mental and physical disabilities don't count. Mere ugliness doesn't count. Morbid obesity does count, though it might not be featured on the site unless that person also has some other losing qualities going on (a mullet or a face tattoo, for example).