Dear Prudence: Using work email to respond to a Craigslist personal. Oops.

Help! I Responded to a Craigslist Personal Using My Work Email. Will I Be Fired and Divorced?

Help! I Responded to a Craigslist Personal Using My Work Email. Will I Be Fired and Divorced?

Advice on manners and morals.
May 23 2013 6:15 AM

For the Private and Confidential Use of the Recipient

I responded to a Craigslist personal using my work email. Will I lose my job—and my wife?

Emily Yoffe.
Emily Yoffe

Photo by Teresa Castracane.

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Dear Prudence,
I am a young attorney at a solid law firm. I work very hard, have received stellar reviews, and seem to be well-liked. I'm also happily married to a beautiful woman I adore. And now I am worried about losing the love of my life, my job, or both. Despite my great marriage, I sometimes peruse Craigslist personal ads, just for kicks. Sometimes I even reply—always from an anonymous email—but it never goes any further than that. It’s just a fun fantasy for me. No hookups, no chat, nothing. I have not and would not cheat on my wife. Unfortunately, this past weekend I replied to an ad from my iPhone and I accidentally used my work email account. Although the email wasn't explicit, it makes me look very bad. I feel absolutely awful. I pay for the phone, but the email goes through the firm's server, which I know has monitoring software. I'm wondering whether and who I should tell about this. I'm afraid if I bring it up at work, what may have gone unnoticed will become an issue. Also, should I give my wife a head's up, in case I lose my job? I'm worried that what I thought was a fun little secret is now going to turn into a very public nightmare.



Dear Saboteur,
Please tell me your cheeky reply did not have an attachment with a photograph of you in the bathroom, bare-chested and flexing your biceps. Yes, you messed up, but at least you’re not running for mayor of New York, so you don’t have to babble to the world about the embarrassing things you did with your electronic devices. Counselor, I counsel that you just sit tight. Sure, for the foreseeable future every time someone from the firm says, “Can we talk?” you’ll wish you were wearing Depends. But you just need to live with your anxiety and hope that your little missive didn’t include any key words that would alert your company’s no-no software. There’s a good chance nothing will happen. So staying quiet and hoping that’s the case will be a lot better than pre-emptively confessing and forcing your firm to deal with your poor judgment. If someone does come to you, then of course you have to own up. Explain this was a one-time, accidental misuse of company email and that it will never happen again. You may be able to walk away with a reprimand. As for your wife, I’m going all in on keeping your mouth shut. I believe you when you say you get a kick from reading naughty ads and occasionally sending a naughty reply, but that you don’t follow up and exchange numbers let alone bodily fluids. One great thing about my job is that people reveal to me their private acts, and I have heard from married men who say they blow off steam, as it were, by cruising sex ads, but nothing more. Even so, if my husband came to me with this confession, I’d probably be suspicious it was something of a cock-and-bull story and that he was withholding the most interesting details. If your job goes kablooey, of course you have to tell your wife all. But right now I don’t see a reason to shake the foundation of your marriage. As it is, you’re getting a good dose of punishment for your transgressions. If you find yourself contemplating your fate at 3:00 a.m. night after night, get a prescription for Ambien. In order to carry on as if nothing’s wrong, you need a good night’s sleep.


Dear Prudie,
I'm a successful and happily married woman in my early 30s with my first child on the way. However, growing up wasn't the easiest for me. From a young age my bad skin, thick glasses, and gawkiness brought ridicule from my classmates. I immersed myself in studying, which made me more of a target. I've realized children can be cruel and have worked to get over the taunting I suffered. What I am not able to forgive is the teacher who bullied me for three years starting when I was 11 years old. She was a young teacher who seemed to be interested in appearing cool to the popular kids. This woman took every opportunity to publicly humiliate me. If I was the only one to raise my hand, she'd call me a know-it-all. If I didn't raise my hand, she would make a snide remark about my not knowing everything. She made sure to point out to the entire class every time I didn't get 100 on her tests and read aloud the questions I got wrong. My mother was a teacher at the school and I told her about this, but she said I was being too sensitive. It didn't help that my older sister had a wonderful relationship with this teacher. For a long time I thought maybe I was too sensitive, but after reading your column I've come to realize that there are people like this teacher who find the lone outcast child and bully them. This teacher was diagnosed with cancer last year and my church did a fundraiser for her. I refused to attend or donate. My mother said I was being cheap and spiteful. Then recently I saw this teacher at church. She looked terrible. She came over to my family and hugged my mother and sister. When she stepped in to hug me, I backed away and excused myself. My mother is now very upset with me for being rude, saying I embarrassed the family, and I should just get over whatever I "think" she did to me. In my anger, I told my mother this woman probably got cancer as punishment for being a horrible person, and the sooner she dies the sooner she can go to hell. Now my mother isn't speaking to me. My husband is on my side and says I should not apologize to my mother, since I didn't wrong her in any way. This isn’t the first time I’ve not been on speaking terms with my mother, but she and my sister are planning a baby shower for me. I want to get past this, but how can I mend things with my mother without apologizing?

—Former Bullying Victim

Dear Victim,
I can understand your anger; it was as if both your mother and this teacher conspired during your childhood to make your life a misery. What a betrayal on your mother’s part to side with her colleague over her own daughter without even investigating your complaints. As for this awful teacher, I don’t blame you for refusing to contribute to her fund and shrinking from her touch. But where you could start in reconciling with your mother is in addressing what you said about her colleague. You’re a well-read woman, so you know that suffering is often unjust—you were a victim of it yourself. This woman’s cancer is not a punishment for her acts. As inexcusably dreadful as she was to you, to wish aloud for her death is ugly to hear and poisonous for you to say. Your troubled relationship with your mother encompasses more than just this teacher. Particularly now that you’re about to be a mother yourself, it would be a good idea to unspool your feelings with a counselor. But for the sake of smoothing over this situation, you can say to your mother that while it’s simply a fact that your former teacher treated you abominably, you do regret wishing her ill. If that’s not enough to get your mother talking to you again, then you have a lot of thinking to do about another bully in your life.