As I (very reluctantly) approach my late mid-twenties, I can't help but think back on the many conversations I have had over the years. However, more than this, I can't help but regret the ones I didn't have. That's what this book is about. It is a collection of conversations that I could have, would have and should have had but didn't because they were too difficult or too awkward or too honest. This is an assortment of 100 letters to different people, things and situations I have encountered in my 25 years of life. Some are quite heartfelt while others make for a good laugh. Through these letters, I document the best, worst and okayest moments of my life. Finally, while I still have the folly of youth as a plausible excuse, these are my honest thoughts on: Family, Friends, God, Boys, People, A Million Little Things and it my greatest hope that anyone reading this finds a bit of themselves in these pages.