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So You Want to Break Up . . .
over the Phone

When It's Appropriate
If you're dating long distance and need to do the deed before you're going to see your soon-to-be ex in person, the phone might be the way to go. It's also understandable to want to break up on the phone if you've gone on a few dates with someone, or had sexual relations with him after one or twelve beers, but never had any intention of actually being in a relationship. Intention is critical here. If you never felt emotionally involved, if this was always just a fling, feel free to dial away.

What's Good about It
Sometimes it's easier to say things over the phone that you can't say in person but need to say in order to make the breakup final. And, when someone is crying over the phone, it's not as sad. Plus, if it goes on too long, you can hang up and blame it on a bad connection. Also, there's the possibility of phone sex . . .

What's Bad about It
Besides the fact that it's morally repugnant, absolutely nothing.

Things to Keep in Mind
The person on the other end of the line can tell if you're not paying attention, and can hear if you're typing e-mails to your new love interest. The bigger issue is that if you care about someone enough to have a conversation with her or him about your breakup, you should care enough to be doing it in person. Even more important, you never know who is listening, like her mother, or the government.

So You Want to Break Up . . .
in a Letter

When It's Appropriate
It's pretty much always appropriate to break up in a letter if the relationship was a meaningful one. At the same time, it's always inappropriate to break up using a postcard with a picture of a hot woman or man on the beach under the sentence, "Wish you were here (not)."

What's Good about It
A letter allows your thoughts time to breathe, and it lets you explain without interruption. The recipient can read it over and over again and really process the reason you are ending things. If well written, it will be something the recipient may eventually cherish. You can also use it as an opportunity to practice your cursive.

What's Bad about It
Most people in the modern world can barely string a sentence together. If you can't spell breakup without spell-check then, well, you better make sure to use spell-check. Otherwise, stick to the phone. Keep in mind that a breakup letter should be poetic, not a string of clichés. If you're not going to be able to do it right, don't do it at all. Also, there's the difficulty of deciding how to sign off. You can't do "Sincerely" or "All my best," but you also can't do "All my love" or "Forever yours."

Things to Keep in Mind
Sometimes someone will draft a breakup letter with the original intention of using the letter as a reference during an actual in-person breakup, but then it starts to seem like it would be easier to just mail the "notes" or hand them to the soon-to-be ex. This isn't recommended. If you're going to take the trouble to write a letter, make it as elegant as you can -- no one wants to receive a stack of three-by-five-inch index cards with the alphabetically categorized reasons they're getting dumped. When breaking up via letter, it's ideal not to mail the letter since you never know if it could get lost, but to leave it where the recipient can't miss it, and to make sure your soon-to-be ex knows you're available for an in-person chat after he or she has taken a few days to think about and/or burn the letter.