When you wake up at 3am and start looking through old emails trying to find something, but end up going in a completely different direction…

• In 2000, the MIT Admissions Office used to ask for your Social Security Number in order to sign you up for their email list.
• In high school, my favorite cheese was “the orange spreadable stuff”.
• In 1999, I was really impressed by a new payment service from X.com called PayPal.
• Back then I spent an inordinate amount of time thinking and worrying about life and the pursuit of happiness. So not much has changed on that front.
• At some point my parents hosted a 40th birthday party for a friend of theirs that involved a male stripper. It was something I said I wouldn’t soon forget. But luckily, I have.
• It’s great convincing your friends to use PGP email encryption, until you want to read those emails a decade later and no longer have the secret key. I can only assume those screenfuls of random gibberish hide the best secrets of all.
• Sometimes when I was 16, I could be completely oblivious and mean.
• Sometimes I could be incredibly thoughtful and caring.
• I can no longer remember at what point my best friend from high school and I stopped talking, or why. I have a vague recollection that we had a big fight, that I did something terribly wrong. But looking back at these emails, I’m increasingly convinced that we just naturally drifted apart. I’m not sure which possibility is less satisfying.