The last month of my senior year of college, I decided to make money on a weekend trip home. I posted my planned journey on a website two weeks out, and two people messaged me wanting a lift. The one agreed on $10 for me to drop her in Richmond, and the other, who we'll call "Pip," agreed on $20 for me to take him to Virginia Beach. Plus, my dad would probably give me gas money, so I was gonna make out like a bandit. Ka-ching, ka-ching.

Slightly before this trip, I had committed to graduate school in Richmond and created a roommate profile on another site. The weekend before the trip, a potential roommate messaged me asking if I'd be interested in meeting and seeing his place. I said yes and figured I could drop off the first person and I'd just tell Pip he needed to find another ride and he could keep his $20.