Relationships, dating
Credit: Illustration by Christian Dellavedova

In my thirties, at an age when many of my friends felt their lives were just beginning, I felt mine was over. I was a man who had found love at a young age, got married in my early twenties, and thought I had the perfect life. I was a rock critic who got to spend every waking moment listening to the music I loved, living with another writer who shared all this music and joy with me. It all changed abruptly, when she died suddenly, in May 1997. Without her, everything was different.

When I started dating again, after three lonely years as a widower, I learned that I did not know much about how to be a boyfriend. Let me rephrase that. I knew nothing about how to be a boyfriend. I have no idea why I was so shocked about that – after all, I'd spent my twenties married. But I was devastated to learn that (brace yourself for a surprise) starting a new relationship is hard. Being a boyfriend is much, much harder for me than being a husband. There isn't even much overlap in the skill set.

I am an Irish male. If you know anything about Irish males, you know there's something we usually have in common: We don't want to talk about it, whatever problem "it" may happen to mean at the moment. "Not talking about it" is one of our specialties, right up there with "talking about everything else except it."

We like to imagine the women in our lives count on us to be dependable, resilient, cool in a crisis – yet that is partly why they can also find us exasperatingly cautious. We don't ask for help. We like to ignore our problems and hope they go away. A few years ago, my Uncle Dermot back in County Kerry got gangrene on his leg and didn't see a doctor for six months. He just kept working the farm and waiting for the leg to get better. When it turned purple, he finally showed it to my cousin, who dragged him to the hospital. They managed to save the leg. To Uncle Dermot, this proved he was right to put it off until the right time. I'd be lying if I said I didn't relate.

The men in my family take pride in not losing their shit, and my early conception of what it meant to be a man as opposed to a boy had largely to do with managing your temper and handling your grievances one at a time. (Little boys – they're petite rage queens, or at least that's how they seemed back when I was one. When I try to remember the boys from elementary school, they blur into one long 'Real Housewives' marathon.)

When I was into my teen years, my grandfather had one of his buddies from the New Haven Railroad over for tea. When I came in to say "Hi," the railroad guy said something along the lines of "Your grandson is very tall." My grandfather said, "Yes, and he doesn't fight, either." He nodded proudly. This was a very strange comment to me at the time. This was the way old Irish men talked when they were bragging about their grandsons? He was proud of me for not getting into fights? I was under the vague impression that this was one of my more eccentric character quirks. He didn't say, "He doesn't drink," or "He doesn't smoke," or "He gets good grades." He said, "He doesn't fight," and that blew my mind at the time. In my grandfather's eyes, that meant I was a man.

Eventually, this was how I came to see husbandhood. Part of the job is keeping a cool head and not overreacting to temporary crises. Again, I'm not trying to defend this pathology. I'm just trying to be explicit about it. And I'm aware it's a pathology that can make for a truly terrible boyfriend. It's one of the reasons I'd rather be a husband.

After all those years as a husband, and a few as a widower, I decided to try couplehood again, even though I wasn't sure I was ready yet. I'd been on the shelf too long. The grief still clouded my heart. But I met a really cool woman who lived across the country. On weekends I flew out to the Midwestern city where she resided (let's call it "Minneapolis"), except we had this fundamental incompatibility (let's call it "me being a bitch"). Was I out of practice, or just still hung up on the past? Either way, I had never experienced relationship troubles like this, and I was a total amateur trying to resolve them. She was a good person. I was a good person. We didn't get along. It was a shock to me after years of being happily married: failing as a boyfriend. What a letdown. It must have been how Michael Jordan felt when he left the NBA for baseball, only to discover he couldn't even hit the minor-league curve.

On Sunday nights I flew back to New York in a miserable mood. At the Minneapolis airport, before my flight, I would drift over to the game room with the South Park pinball machine. I began making excuses every Sunday so I could get to the airport earlier. I would spend hours at that South Park machine, with my carry-on bag and my boarding pass, and think, "Maybe this is who I am now. I used to be good at being somebody's husband. I made a woman I loved smile for a few years. I had a nice run, but it's over. This is me now. The guy who's good at playing pinball in airports."

After we broke up, she mailed me a present for my birthday: a box of brownies. Not a baked batch of brownies – a box of Duncan Hines brownie mix. A strange gift, maybe, yet it was an incredibly kind gesture, and it made me really happy. I displayed the box on the kitchen counter, where it brightened up the room for a few days. In a way, it was the ultimate compliment – a sign that someone saw unbaked potential in me. Even in my shaky emotional state, somebody had high hopes for me, to the point where she could picture me taking on a project like opening a box of brownie mix and shopping for eggs and finally turning on the oven I used for storage space. But it was not to be. When my birthday rolled around, I spent it at home alone, in front of the TV, watching Britney Spears and LL Cool J host the American Music Awards. Midnight came. I was 35. I threw the brownie mix away.

All the things I thought I had already learned about love? I didn't know a thing. I was going to have to learn it all over from scratch.