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The question

Three years ago, I instigated a falling out with a close friend. She never saw it coming and was hurt. We haven't spoken since, but I've always felt guilty for blindsiding her, not fully explaining my motives and doing it while she was mourning her father. It's probable she blamed herself and thinks I despise her. The truth is quite the opposite: She needed support, and I misled her (and me) to believe I could fill a role. As we grew closer, I realized what little of substance we had in common. Not knowing what to do, I killed the friendship. Lately I considered reaching out to her, not to reconcile, but to give her the opportunity to chew me out or get answers. Is there any point? All indications are that she has moved on with her life.

The answer

I do think there is a point to reaching out to your friend, even though it's been three years. True, it's a long time. But better late than never! In my twenties, one of my friends had sex with my then-girlfriend in the bathroom at a party. Meanwhile, I was standing outside the door, waiting to use the facilities, clueless.

"Whew, whoever's in there sure is taking their time," I said to a group of people nearby. I still remember the pitying looks on their faces. To this day, I wake up in the middle of the night, moaning, clutching my face, rocking back and forth, recalling their expressions.

I broke up with her, and didn't speak to that dude for more than a decade. But I forgave him in the end. And I'm glad. He's an important person in my life. Our kids play together. Those guys we were – the one with his pants around his ankles inside the bathroom and the one with a stupid look on his face standing outside – well, they were just different guys.

Now, I know sometimes a friend can do something so egregious you have to drop them. In the age of Facebook, it sounds easy. Press a button, poof: defriended.

But in reality, carrying around a "killed" friendship weighs heavy on one's soul. It's the psychic equivalent of humping a dead body around on your back: Only when you slough it off do you realize what a heavy burden it was.

And it doesn't sound like your friend did anything too bad. In fact, it sounds like you have quite a bit on your own conscience. Good! So many people who write to me are quick to point the finger of blame, never considering that most of us tend to be the authors of our own misfortune.

So yes, reach out to your friend. Not by e-mail. E-mail, as I have learned from bitter experience, is the wrong medium for expressing anything from the more negative/choleric end of the spectrum of emotions. I don't know why, but tempers flare fast and burn hot online.

Phone her and suggest a get-together. Tête-à-tête is by far the best means to effect a rapprochement.

Apologize for whatever is on your conscience – at the very least, poor timing and misleading her, sounds like – and avoid the temptation to reproach herwith anything. That's for later. Reading between the lines, it sounds like maybe she was leaning on you a little too heavily for support? But worry about setting those kinds of boundaries down the line.

On this occasion, you're just smoking the peace pipe. If she rebuffs you, be placid and patient (within reason). She's probably got a little ball of bile she has to cough up, like a cat with a furball: Afterward, she'll feel better.

That is all presuming this friendship is important to you. And I sense it is. Otherwise, why would you have written in? Who cares if you have little in common? My male friends are all enraptured by sports, about which I'm clueless and couldn't care less. But we still have a good time, and love each other. Even if you don't wind up as close as you were, even if you wind up more friendly than friends, it's for the best.

Think of the bigger picture. Not to sound too Shaolin/Kwai Chang Caine from Kung Fu on you, but I think you'll find yourself treading lighter as you walk the earth. And afterward, well, that's one more person genuinely sorry – and not experiencing mixed emotions – to see you go. One more person to speak from the heart, and not through clenched teeth, when delivering your eulogy.

What am I supposed to do now?
