“That’s what told me, ‘I think I’m going to be O.K. not having kids,’” she said. “Since I was 25, I had been dating to find my baby daddy. But I had done therapy and other kinds of personal work. I finally accepted that my mother had died, that my family wasn’t what I wanted it to be, that I wasn’t a skinny model. And I started to have fun. It was a new thing for me, not feeling like each person was my last best hope, but rather there’s more where that came from.”

At the same time, Mr. Rosenberg was on his own journey of self-discovery. “I’d considered myself relationship-phobic,” he said. “I was ready to become a monk. My whole thing is not being able to trust — I can’t take it if I go into something and give it my all and it doesn’t work out. After a lot of work, I got to a point where I was ready to open up. That’s where Jen came into my life.”

They met on OkCupid on Dec. 29, 2015. While Ms. Bilik (alias: WittyWarmWise) had been online dating on and off since the early aughts, Mr. Rosenberg (alias: drschauffhausen) only had to dip a toe into the quagmire before meeting his future wife. In fact, he received a message from Ms. Bilik five minutes after joining the site. “I got lucky,” he said with a smile.