How to Dump a Guy Without Upsetting Him

Plan. Choose a neutral date—try to give a week or two buffer time between birthdays or anniversaries if you can. Start to show subtle signs that you're less interested—don't tell him you love him out of the blue, act slightly distant when you're together etc. Be careful here; there's a fine line between giving subtle signs and being a jerk.^[3]

• If you've told a friend, tell your friend exactly when you plan on breaking up. Call them just before you see your boyfriend so that they can give you extra courage. This will ensure that you go through with the breakup instead of dragging it on for weeks (which is not fair to you or your boyfriend).

Plan a neutral but relatively private location, such as a less-than-crowded park. If your breaking up with someone long distance, make sure it's a day when you know they'll be available to talk on the phone or Skype alone.^[4]

Prepare yourself emotionally. When the time rolls around, don't chicken out. Tell yourself that you're doing the right thing—not only will you be happier after you break up with your boyfriend, but it's not fair to him to be with him if you're not happy. Refresh your mental list of the reasons you're breaking up. Talk to your friend for support before you see him if you need to.^[5]

Greet him. You will be nervous, but don't just launch into the breakup. Give him a friendly hello and a smile. If he starts talking to you, don't panic. Sometimes a little small talk before you drop the bomb will help ease the situation. Don't force small talk either, though. When there is a lull in the conversation, take a deep breath. Tell him that you think that the two of you should split. The exact wording is less important than the fact that you should get the point across. This sentence is not the time to be sympathetic or apologetic—make sure your tone of voice is polite but assertive.

Encourage talking. Your boyfriend's first instinct may be to leave or say something rude. Keep a level head and ask him to talk it out before he gets angry. Give a couple sentence summary of why you want to break up. Apologize. Then, let him ask questions. He may be feeling overwhelmed, so don't be alarmed if he doesn't have much to say.^[6]

• If your boyfriend asks why, do not give him a detailed list of everything he's done wrong. Try to keep it along the lines of "my feelings just faded, sometimes it happens." If he wants specifics, it's okay to give them, but be sensitive. He shouldn't feel like you're attacking him.

Allow the conversation to flow its course. Above all, try to stay calm. He will feed off your energy. When you sense that the conversation is nearing its end, explain to him that you really do want to get to the point where you can be friends again. However, you should also make it clear that you want to give him adequate time to get over you. Therefore, he will have to make the first move towards friendship if and when he's ready.

• Let him know that you really enjoyed your time together. This will help him remember that he did mean a lot to you—that the whole relationship wasn't pointless.

Say goodbye. Once the two of you part, avoid contacting him unless he contacts you first. Don't talk smack about him to your mutual friends, and try not to make anyone take sides.^[7]