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After a few minutes of browsing, the tell-us-about-yourself questions took over the screen; answering a certain number allowed you to browse again. DateDate defied all rules about how to make an engaging app—“so much friction,” one early reviewer in TechCrunch stated—and yet our userbase continued …

It seemed Allie didn’t know many people at the meetup, either. Her roommates were alums of Ivy League universities, and most of the people here were recent transplants from “back East,” thrilled to be in “San Fran.” Allie suggested we take a walk. On our way out of the apartment, I overheard one gu…

At the bar, someone was singing Robyn’s “Dancing on My Own,” a song I would never stream on Rdio because it wasn’t compatible with my publicly visible aesthetic preferences, but which I secretly loved. The mood of the song made me feel expansive.

He cracked open a Red Bull. “The VCs want us to hire more engineers, maybe a designer. But we might be able to bring on a contractor to help you for a few months.” He took a swig and switched into his friend voice, the looser cadence I remembered from our early days together, right out of college, …

Content review, I corrected, a term that cast the work as more professional, at least in my eyes. I added that I also helped implement clever in-app solutions for users struggling with serious issues: cutters and anorexics, the depressed and the bullied. If you included “suicidal” in your dating pr…