Who Pays? When you start going on several dates, the issues about who pays can shift from the routine you have set up on your first dates. As you go out more often and spend more money, you might want to share more equally in some of the expenses. And you might want to be more sensitive to who is earning more money. Talk about this without fear, because not doing so has some unpleasant consequences. For example, he might not ask her out to a nice place -- or to go out at all if he doesn't have the money, leaving her thinking that he doesn't care about her when really he is ashamed or simply cannot afford it. To avoid the problem of too-expensive dates, plan a few activities that do not cost much. For example, go to free concerts in the park, go for a drive, visit museums, or hang out with friends.