Probably the worst part about all the great technology we use to communicate with one another is the ability it gives us not to communicate with one another. Rarely will a text message accomplish what a conversation can. Which is why you should never, ever, not ever break up with somebody via text message. (There are a few possible exceptions to this rule.)
We send and receive texts seemingly at random. We never know when to expect a text message; they pop up out of the blue. A conversation, at least, you can prepare yourself for. But it's a little cruel to send a "We need to end this" text message without knowing what the recipient is doing at that specific moment. It's a fine way to ruin your soon-to-be ex something's day at the beach. Or, you know, whatever.
Plus: It's bad enough to hear those fatal words in the back of your mind, over and over, while you mope. But to have those words written out and saved in your phone—unless you delete the message, which takes a considerable amount of strength—is painful. Because, in the same way you're going to replay the words in your head, you're of course also going to keep returning to that text. Reading it, and rereading it. Trying to decipher some new, more optimistic meaning that really is not there. It's like a souvenir of a broken heart. And if you care or cared about this person at all, you wouldn't want to give them something to torture themselves with.
This doesn't mean technology should be absent from this sort of...occasion(?) If you're not both in the same place when it comes time to have that talk, you could talk over Skype or Google Hangouts. Give the other person the courtesy of seeing your facial expressions, hearing your voice and the nuance in it when you explain why it is just isn't working. At the very least, pick up your phone and dial their number.
A text is a cop-out, a grenade you can throw from a safe distance. They'll want to talk about it anyway—probably—so just have the conversation. Save the texting for less serious stuff. Or booty calls.
Original illustration by Robert Grossman.