“Great,” I respond. Of the many, many dating apps and sites I’ve worked with, it’s actually one of my favorites. The interface is pretty simple and intuitive. And matches are conveniently already sorted into three categories: Game (hookups), Set (a catchall for those who aren’t sure what the hell they want), and Match (long-term relationships). “Okay if I access your computer?”

“All yours, chief,” he responds.

I click to the remote access program that I already had Jude install on his computer, wait for him to “accept,” and then, voilà, his screen is up on mine. He already has the browser open to Game Set Match and I can see the notification that he has one message. I click through.

It’s from someone named RayaJack5, whose profile picture is ostensibly of the large cross she apparently wears around her neck, but is, in fact, mostly of her rack.

RayaJack5: Hey. Seems like maybe we’d be a match, so wanted to say: hey.

I see she’s in the “Set” category. Well, better than “Game,” since Jude and I’ve already established that he’s looking for more than that.

“Okay,” I tell Jude. “So, basically, she’s leaving the ball in your court. Which is pretty common.” Sometimes, people word vomit on the initial contact, trying to get everything that they’d ever want the other person to know about them across in a cramped, convoluted block of text that—more often than not—just reeks of desperation. That’s only slightly better than the absolutely infuriating “hey.” At least Raya added a bit more flair to hers than that.

“So should I write back . . . ‘hey?’ ” Jude asks.

“Um, no,” I respond. “Because think about it. What would ‘hey’ accomplish exactly?”

Jude shrugs. “Don’t know.”

“Exactly,” I say. “Think of it this way: Every interaction should have a purpose, however small. Whether it’s to get to know more about the person, make them laugh, flirt with them, tell them more about yourself, etc. Everyone’s busy, right? Why waste your time or someone else’s time on something that’s obviously not going to work? You ask the right questions, and you won’t have to.”

Jude laughs. “That might be the most New Yorker thing I’ve ever heard anyone say.”

I shrug. “Maybe. But it works.”

I see Jude looking at Raya’s message again before turning his attention back to me. “All right then. So what would you say?”

“I’ll type it on your screen, and if you like it, you hit send, okay?” I can always get my thoughts together better in writing.

“Sure,” he responds.

“Give me a minute to check her profile out,” I say.