When I was 25, I spent a year dating a man 20 years older than me. The Older Man was also my editor, which added a power imbalance to the mix—a dynamic we all know can be equal parts problematic and irresistible. I wonder: What do we gain and lose from dating someone of a different generation? The Older Man was a peculiar person. For one, he wore silk onesie pajamas that he meticulously ironed to have a crease down the center of the pant leg. For instance, we were both making our first attempts at writing books. Dating up had its perks. He also taught me what a k was.