He has a loving wife, a small child—and sex with men on the side. How the Internet has made it easier than ever to lead a detection-proof double life.

The man sitting across from me would like to tell me his name, but doing so is against his rules. He could tell me a fake name, he says, though not the one he typically uses when meeting a man in the middle of the day, since he has been using the same fake name for so long that it is almost real. Revealing it now would open him up to the potential of recognition, and, frankly, just imagining a scenario like that makes him wonder why he agreed to meet in the first place. He knows how he comes across. So shifty and paranoid. But he is not apologetic. Because when you live two separate lives, as he does, and when you have been maintaining these two separate lives for twenty years, as he has, coming across as shifty and paranoid is something of an inevitability.

I will call him William Dockett, for clarity’s sake. Over the past few weeks, William and I have been e-mailing regularly. This is what I know about him: I know that he is in his early forties and that he lives and works in Manhattan, earning around $200,000 annually in a job he wishes he was more passionate about. I know that he is a registered Democrat who grew up in a nearby suburb. I know that he has been married a decade and that he is the father of a small child. And I know—here his life gets complicated—that when he is at work, and things are slow, he goes to Craigslist and, with a familiar mixture of guilt and resignation and excitement, clicks on the “men meeting men” section of the personals.

It is hard to fathom, the notion of a gay man living a closeted life in New York City in 2007. The life of someone like William—who responded to a posting I placed on Craigslist identifying myself as a writer trying to understand the psyche of a still-closeted man—seems at the very least anachronistic. Typically, the “closet” brings to mind small towns, intensely religious communities, and, at the most cosmopolitan level, the lives of Jim McGreevey and Mark Foley: gay men operating in a world so inherently duplicitous that their choosing to lead a shadow life follows, sadly, a certain logic. And yet the thing about desire—frustratingly, thrillingly—is that few things are so resistant to reason and categorization. “I used to think I was bi, but now I really believe that I am gay and just was not in the right situation,” William wrote to me in an early message. “I think I like a particular kind of guy and when I went out looking I never found him, so I gravitated toward women. I found what I liked on the Internet, but I was already married.”

We are meeting at a pub in the West Village, desolate at this midday hour, a location chosen because it is far removed, geographically and psychically, from where William lives and works. He is, as he refers to himself online, “average looking,” medium height, clean shaven, a little stocky but in decent shape. He’s wearing dark tapered slacks, a well-ironed pale-blue shirt, cuff links, and a pink tie that is flashy but by no means flamboyant, knotted half-English style. For weeks he has resisted the idea of talking in person. “I’m sorry,” he wrote, “but my life is a mess right now.” And later: “Why am I even talking to you?” Once he agreed to meet, he warned me, “You’re going to be disappointed. I’ve had to become very good at revealing very little.”

He was not exaggerating. My questions are answered curtly, almost inaudibly. No, he is not religious. No, he was not raised in a religious or bigoted household. No, he does not think being attracted to men is “wrong.” No, it’s not that simple. This much he will allow: “This is not the life I was meant to live. I don’t know what that life is, what it looks like, but I know it’s not this. But I don’t think most people are living the life they think they were meant to live, so I don’t feel that bad.” I walk away from the lunch thinking that the most telling thing about the entire exchange is how little William is willing to tell. His paranoia is palpable, clearly consuming. Whatever the reason he decided to meet me in the first place—vanity, a desire to tell a few of his secrets, maybe even a subconscious wish to be discovered—I feel certain that he will not wish to meet again.

But later that afternoon he sends me an e-mail: “I think I want to keep talking to you. I don’t know why, but I do.”