How to write a "Dear John" letter

a person writing a dear john letter

Writing a “Dear John” (or Jane) letter seems to be a dying concept. It may not be the most pleasant letter you ever write, but it demonstrates maturity and consideration for others. For those of you unfamiliar with the term, a “Dear John letter” is written to break off a relationship with one’s significant other.

How to send it

It’s not an easy letter to write. But it is only good manners to explain your decision. After all, at some point in the relationship you valued the feelings of this person. Facing the issues that divided you squarely and honestly will make the breakup easier to manage for both of you.

A popular commercial would suggest that sending a text or email is appropriate for this important message. Especially if you can do it using your free minutes. While it makes good ad copy, it doesn’t show much concern for the other person’s feelings and dignity. This is a message best received and read in private. Consider a hand delivered note or mailing through the not-yet-obsolete US Postal Service. It’s worth the fifty cent investment (adjusted for inflation).

Consider the social and work context

If your soon-to-be ex is in the same workplace or part of the same social group, your task may be more difficult. If office romances are tricky, office breakups are even worse. Especially if one of you is the direct superior of the other. Your Dear John letter should place job considerations above the romance. In these situations, it is extremely important to demonstrate your maturity.

While disturbing the dynamics of a group of friends doesn’t quite have the same impact as a work-related break-up, some of the same issues apply. A tightly-knit social unit can be devastated by the split of one of its couples. As in a divorce, friends tend to “take sides.” It will probably be impossible for both of you to participate in the same group from now on. There are exceptions. If the breakup was civil and cordial, you may both be able to continue those all-important friendships. Hence, the need for a carefully worded Dear John letter.


Depending on the nature and length of the relationship, the letter may be short and sweet or long and detailed. Address the main issues that resulted in the breakup. Emphasize your own feelings and opinions. Avoid attacking the other person. “I don’t feel I’m able to be myself in this relationship” is much better than “You’re selfish, immature, and controlling.”

Be as specific as possible. Expand on the “not being myself” idea from the previous paragraph. Say that you feel that the other person usually decided which activities you would take part in and that you felt obligated to please him or her whether or not it was something you wanted to do. Take this use of details to the next level by giving a specific example: “I was terrified to go bungee jumping, but I felt pressured into it.”

Positive changes

If you do a good job with your good-bye letter, you may wake up your friend to some character flaws. In the best-case scenario, the breakup may result in some changes for the better in the other person’s life. Or in your own. Every false step offers opportunities for growth. Examine your own part in the discord in the relationship. Admit the problem was, at least, in part, your own fault. Word this part carefully. Don’t open up new wounds by confessing something your partner wasn’t aware of. Avoid making yourself the target for bitterness or blame.

Make your decision clear

A Dear John letter could easily be misinterpreted. Your partner could take it as an ultimatum: Straighten up or else. He or she might think of it as an offer of a second chance. It may even be looked on as an apology on your part. Or, in an extreme case, it could be viewed as a threat.

Make sure that your intentions are clear. You have thought this through and it is over. Period. You are writing this letter as a courtesy. But it is over. Definitely over.

In summary

Be specific. Be kind. Be firm. Then brace yourself for the response. All your efforts to tactfully present your feelings may be lost on a person who feels deeply in love. Avoid the temptation to meet with the person to “talk it over.” You may find yourself being coerced into starting over. Which, in some cases, might be a good thing. Or it could mean getting back into a destructive relationship. Just give yourself some time to think it over.