But it’s hard, it’s so hard, because we’re not taught how to ask hard questions of both ourselves and others. We believe that social reality is more important than individual reality, that being with someone who makes you look good is better than being with someone who makes you feel good. And we live in a time where we have more optionality and less transparency than ever before, where changing social norms have created highly competitive marriage markets (more on this later). That is, as far as I can tell, why dating hurts.