It wasn’t easy being the guy who was perfect for someone else. It often left me brokenhearted, and I couldn’t understand why women told me that they wanted certain traits – romance and kindness, interest and the ability to listen – and then didn’t appreciate it when it was actually offered to them.

I wasn’t altogether unlucky in love, of course. In high school, I had a girlfriend named Angela during my sophomore year; in college, Victoria and I were together most of my junior year. And during the summer after graduation from college, when I was twenty-two, I met a woman named Emily.

Emily still lives in the area, and over the years, I’ve seen her out and about. She was the first woman I ever loved, and since romance and nostalgia are often intertwined, I still think about her. Emily was a bit of a Bohemian; she favored long flowered skirts and sandals, wore little makeup, and had majored in fine arts with an emphasis on painting. She was also beautiful, with chestnut hair and hazel eyes that were flecked with gold, but beyond her physical appearance, there was more. She was quick to laugh, kind to everyone she met, and intelligent, a woman who most thought was perfect for me. My parents adored her, Marge loved her, and when we were together, we were comfortable even when silent. Our relationship was easy and relaxed; more than lovers, we were friends. Not only could we talk about anything, she delighted in the notes I’d place under her pillow or the flowers I’d have delivered to her workplace for no reason whatsoever. Emily loved me as much as she loved romantic gestures, and after dating her for a couple of years, I made plans to propose, even putting a deposit down on an engagement ring.

And then, I screwed it up. Don’t ask me why. I could blame the booze that night – I’d been drinking with friends at a bar – but for whatever reason, I struck up a conversation with a woman named Carly. She was beautiful and she knew how to flirt and she’d recently broken up with a long-term boyfriend. One drink led to another, which led to more flirting, and we eventually ended up in bed together. In the morning, Carly made it clear that what had happened was simply a fling, with no strings attached, and though she kissed me goodbye, she didn’t bother giving me her phone number.

There are a couple of very simple Guy Rules in this sort of situation, and Rule Number One goes like this: Never ever tell. And if your sweetheart ever suspects anything and asks directly, go immediately to Rule Number Two: Deny, deny, deny.

All guys know these rules, but the thing was, I also felt guilty. Horribly guilty. Even after a month, I couldn’t put the experience behind me, nor could I seem to forgive myself. Keeping it secret seemed inconceivable; I couldn’t imagine building a future with Emily knowing it was constructed at least in part on a lie. I talked to Marge about it, and Marge was, as always, helpful in that sisterly way of hers.

“Keep your stupid trap shut, you dimwit. You did a crappy thing and you should feel guilty. But if you’re never going to do it again, then don’t hurt Emily’s feelings, too. Something like this will crush her.”

I knew Marge was right, and yet…

I wanted Emily’s forgiveness, because I wasn’t sure I could forgive myself without it, and so in the end, I went to Emily and said the words that even now, I wish I could take back.

“There’s something I have to tell you,” I began, and proceeded to spill everything.

If forgiveness was the goal, it didn’t work. If trying to build a long-term relationship on a foundation of truth was another goal, that didn’t work either. Through angry tears, she stormed off, saying that she needed some time to think.

I left her alone for a week, waiting for her to call while moping around my apartment, but the phone never rang. The following week, I left two messages – and apologized again both times – but she still wouldn’t call. It wasn’t until the following week that we finally had lunch, but it was strained, and when she left the restaurant, she told me not to walk her to her car. The writing was on the wall and a week after that, she left a message saying it was over for good. It crushed me for weeks.

The passage of time has lessened my guilt – time always does – and I try to console myself with the idea that at least for Emily, my indiscretion was a blessing in disguise. I heard from a friend of a friend a few years after our breakup that she’d married an Australian guy and whenever I caught a glimpse of her, it appeared as though life was treating her well. I’d tell myself that I was happy for her. Emily, more than anyone, deserved a wonderful life, and Marge felt exactly the same way. Even after I’d married Vivian, my sister would sometimes turn to me and say, “That Emily sure was something. You really messed that up, didn’t you?”

I was born in Charlotte, North Carolina, and aside from a single year in another city, I’ve lived there all my life. Even now, it strikes me as almost impossible that Vivian and I met in the place where we did, or even that we ever met at all. After all, she, like me, was from the South; like mine, her job required long hours, and she seldom went out. What are the odds, then, that I’d meet Vivian at a cocktail party in Manhattan?

At the time, I was working at the agency’s satellite office in Midtown, which probably sounds like a bigger deal than it really was. Jesse Peters was of the opinion that pretty much anyone who showed promise in the Charlotte office had to serve at least a little time up north, if only because a number of our clients are banks, and every bank has a major presence in New York City. You’ve probably seen some of the commercials I’ve worked on; I like to think of them as thoughtful and serious, projecting the soul of integrity. The first of those commercials, by the way, was conceived while I was living in a small studio on West Seventy-Seventh between Columbus and Amsterdam and trying to figure out whether my ATM accurately reflected my checking account, which showed a balance with just enough funds to purchase a meal deal at a nearby fast-food place.