Therapists and relationship coaches explain why dating at middle age comes with its own set of challenges. Remember when dating was about meeting a potential mate through a friend and getting to know them over dinner and a movie? Well, if you're dating in your 50s , you know that it can be so much more complicated than that idyllic scene of your younger years. You might be reemerging on the dating scene following a long hiatus, perhaps after being divorced or widowed-only to find that the rules and technology of the game have changed. In fact, there are many particular challenges that come with dating as a something.