Like leather pants, deals with the devil, and Mini Coopers, relationships are incredibly tricky to get out of. Mostly, that's because ending a relationship sucks and there's no good time or way to do it. Trying to plan how to break up with someone without hurting them is like scheming about how to best drop a grand piano on someone's foot.
On top of that, while society has a whole built-in sympathy mechanism for people who have been broken up with, we quickly forget about the person who had to do the dumping, which usually takes a lot of courage and self-inflicts a lot of pain. No one comes over with ice cream because you dumped someone. No one expects you to be locked in the supply closet at work crying again because you realize it's not working out with your partner. It's a lonely, isolating act, and you're the bad guy.
But there are, of course, ways to make it suck a bit less for all parties involved.
Pick a neutral time and place.That means not their birthday, not seven minutes before they're supposed to leave for work, and not while either of you is naked. Again, there's never a good time to break up with someone-it's not like anyone sits around thinking, "Eh, having my heart smashed would be okay right now." You can, however, mitigate the awkwardness of the conversation by picking a private location (don't break up over the phone unless you have to) and a time as far away from any major holidays as possible. No one needs their Aunt Fran probing them about why the two of you didn't work out or to watch another friend get engaged over New Years while they try to not drunk dial you. (For breakups, I suggest August, which is always a bit dull.) In all seriousness, once you know that you need to break up with someone, it's difficult-and rather cruel-to keep going through the motions with them. That said, if you've somehow come to this realization during their PopPop's funeral, keep it to yourself for a bit.
Keep it snappy. When you do have the conversation, don't belabor it, and don't have it more than once. Unless you share custody of something with a longer lifespan than a gerbil, you do not need to keep talking to this person. Maybe you have to send the dreaded, "I'm missing my Nintendo Switch controller; do you have it?" text, but wait at least one month to do so. If you're in the same friend group, your timeline of acting like things are cool between you two might be rushed, or perhaps you see them at work occasionally and must Keep Things Cordial. Fine. But hashing and rehashing the breakup itself only prolongs the pain. So, if your soon-to-be-ex repeatedly asks to talk, it's perfectly reasonable (and, in fact, healthy) to say, "I cannot have this conversation again; I've let you know where I stand. I'm sure that will seem very heartless of me, and I'm sorry." If you're going to be one of those unhinged people who insists on remaining friends with someone whose naughty parts they've licked, fine, but you, the breaker-upper, may not reach out.
Avoid cliché. If you say the words, "It's not you, it's me," I will come set your car on fire with my mind. There's a reason there aren't pithy Hallmark cards to do your breaking up for you: the least you can do when severing a relationship is put it in your own words. Since the dawn of humanity, couples have broken up approximately 900 billion times (conservative estimate). No one is expecting you to pen some brand new, heretofore unspoken breakup soliloquy with new insights into what it means to lose love, but at least tailor what you're saying to the actual situation at hand. Say what you mean, be clear and concise, and get out.