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Ask E. Jean For DearSugar: Help, I'm Being Blackmailed!

Ask E. Jean For DearSugar: Help, I'm Being Blackmailed!

Dear E. Jean,

I find myself in a very strange, very frightening situation. You will not see my real name anywhere on this post, because people are threatening me. I am a good, kind, hard-working 29-year-old woman. I have a wonderful fiancé who is finishing his surgery residency and we are planning a June wedding. Because I made a terrible mistake and carried on a brief affair before I became engaged — it lasted all of one week — with my boss (who is female, by the way), I am being blackmailed by a horrible man at work.

Two months ago he demanded $600 in cash. I gave it to him. Last month he demanded $800 in cash and I gave it to him. (This may not sound like a lot of money to you, E. Jean or to the DearSugar ladies, but I promise you, it was very difficult to find an extra $800.) He seems to be well aware of how much I make, and this month (yesterday on the 15th,) he asked for $1000. He says if I don’t pay him, he will go to the CEO and “out” me and my boss. I believe him.

If he goes to the CEO, I will lose my job and so will the woman with whom I had the affair. What should I do? This can’t go on! I don’t have the money! I will have to go to the bank and borrow to pay him the $1000. Please, please help me. I don’t want my fiancé to find out, I don’t want to lose my job! And I don’t know which way to turn!
— Alias in New York.

To see E. Jean's answer

My Dear Miss Alias,

Go to the authorities. The man marked you out as an easy victim; and all I can say is: He's about to get the surprise of his idiot life! He’s a criminal, a maggot, what he’s doing is illegal, and he will roast his foul carcass in jail for it. Here are the steps to take:

  1. Keep your wits about you.
  2. Behave at the office as you always behave (i.e., don't tip him off that you are about to take action).
  3. Make copies of your bank statements, any threats, any emails that contain even the smallest inference of his asking you for money, and also write down everything that has happened from the first moment he blackmailed you. That means dialogue, time, place — all details.
  4. When you have (quickly!) gathered the evidence (and alas, it sounds like you do not have too much) go to your local district attorney’s office and file a complaint. A prosecutor will then issue an arrest warrant for the guy — or (more probably) set up a sting operation to catch the worm in the act of taking money from you. You can also go to the police, or to your county sheriff’s office.
  5. Now comes the hard part: Alert your friend/boss what is happening. Nobody knows for certain what went on between the two of you, so my advice to you both is: Refuse to admit anything. Characterize the blackmailer’s accusation as “the frivolous wishful thinking of the office schlub.” You and your boss can figure out how to tell the CEO that one of his employees is attempting to blackmail you over something that is “too ridiculous to even imagine.”
  6. And now the really hard part: Tell the truth to your fiancé. But not the details. You can say you had a brief dalliance, it happened before you were engaged, it lasted less than a week, and that you have reported the blackmailer to the police.

Good luck, Miss Alias. Mr. Blackmailing Slimebucket is just about to learn he messed with the wrong woman!

To see more advice from E. Jean visit Elle magazine and

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