In response to your brain weasels, as long as your trying your best and Bruce is happy, he is having a wonderful life. You have more dating experience than most sophomores I know, and more than me, a junior. Don't worry about it. And who cares if your book only sells 15 copies. That's 15 more people who's lives you've touched.
You deserve to be happy. Prove your brain weasels wrong and succeed