Definitely been there. I've obsessed about comments I've made that weren't well thought out and maybe hurt a friend or coworker. It helps to remember that they aren't obsessing about you. They have their own life and probably aren't giving it much thought. If you did hurt him, bringing it up again just reopens a wound that has likely already closed. Just try to re-cultivate the friendly relationship in a natural way and you will get over it in time.