As my first deadline is approaching (Jan.4) I'm starting to get a little uneasy about one of my letter writers (The other two have submitted theirs). I asked him to write it in October and he agreed, but he has yet to submit it to any school. I reminded him in November and again in early December. So now my question is: how many reminders can I send without annoying the daylights out of him? Especially since it's the holiday break, and he probably is trying to relax with his family. Anyone have thoughts/advice?