For Scott Birnbaum, finding Tracy Podell was akin to solving a complex math problem.

Mr. Birnbaum, a data-mad web executive looking for love, found himself taking deep dives into the algorithms and user behaviors that drive some of the largest dating websites. He emerged with a solution for gaming the system to his advantage, creating a profile that attracted Ms. Podell, even if it wasn’t entirely accurate.

Mr. Birnbaum, now 39, considers himself to be “a first-adopter” and a life hacker, whose pursuit of an efficient existence through apps and other gizmos can sometimes infect him with paralysis by analysis. “It took me six months to switch phone plans because I was like, which one is the best?” he said.

He readily admits that his initial forays into online dating were lackluster. While living in Seattle, he found that his friends were getting a lot more hits than he was. So he investigated how he could improve his profile and began tinkering with multiple accounts.

“I started noticing that everybody said the same thing in their bio,” he said. “And I was like, well, I’m not going to stand out very much if I do that. I should write profiles that — while they, you know, weren’t necessarily lying — accentuated different parts of things I was interested in.”