Click—oh, nooooooooooo! (a book contest)


Just sent an e-mail to the wrong person. Hate when that happens.

In the grand scheme, not that huge of a deal. I’m going to be in Chicago next weekend doing some research, so I decided to get a credential to the Bears game and write my column off of it. However, I sent the e-mail that was supposed to go to B.J. Schecter, my awesome editor, to the Bears’ media relations director. Again, a 1 or 2 on the 1-to-10 scale of blunders. But still sorta cruddy.

Along those lines, let’s have a book giveaway. A free autographed copy of Boys Will Be Boys to the person who has the most humiliating I-can’t-believe-I-sent-that-e-mail! story. E-mail them to me at, or post it in the comments section below this entry.


Along those lines, I just thought of a truly humiliating story that I’ll share. Back when I was a young punk fact checker at Sports Illustrated in the mid-1990s, I rubbed a couple of co-workers wrongly—and vice versa. They weren’t bad guys, in hindsight, and neither was I. But we were all ambitious, anxious, probably a tad ornery.

Anyhow, I was single at the time, and some way or another I was trying an early version of online dating. I believe I was exchanging e-mails with a woman over AOL, and she wrote, “So what do you look like?” I didn’t really know how to answer, so I told her a former girlfriend used to say I reminded her of Tom Hanks. (neither compliment nor insult). When we were done chatting, I printed the dialogue out. But instead of landing in my office printer, the paper made it to the hallway printer.

I forgot about the whole thing until, a few hours later, the three guys walked by my office. They were all smiling. Snidely.

“Hey, Tom,” one said.

F***, I wanted to jump out the window.

7 thoughts on “Click—oh, nooooooooooo! (a book contest)”

  1. This didn’t happen to me. It happened to a former colleague. But I’ll claim it as my entry for this contest. Because I love the Cowboys that much.

    Dude wrote a note to his supervisor. Their boss was out for the day. My friend asked his friend/supervisor in the note whether their boss was coming in that day. In place of their boss’ title or name, he referred to her in a way that highlighted her, let’s say, girth.

    He hit Send. Moments later, after peeking at his supervisor’s cubicle for a visible reaction, he asked whether his supervisor had received the note.

    No. Hadn’t seen it.

    My friend’s insides dropped. Shit. Perhaps he’d sent it to the wrong address. Perhaps he’d sent it to their boss.

    The boss leaves his/her e-mail inbox open at all times so assistants can access files when needed. My friend rushed to check for his note.

    There it was, still unopened — maybe their boss hadn’t checked from home yet — and so he deleted it. Then he cleaned the Trash folder. He went back to his desk and recalled the note.

    The boss never saw the note, as far as anyone knows. But that, my friend, is a momentary lapse that many people dread.

  2. I was working in Human Services as a Family Therapist and was asked to go to Chicago (from Iowa) to transport someone back. Figured it would add up to about 6 hours I wouldn’t have to see clients for that week and would be reimbursed for gas.

    Things I was not told…Where in Chicago it was (had to go NOW, will get you the info on the road)…how far up on the gang chain, and connected, the father of the transported to be was. The list goes on.

    I show up outside the pick up spot and call inside to find out which door to go to…telling the lady on the other end that there is 3-4 guys sitting in front of every door and an Escalade had pulled in behind me (with a passenger now knocking on my window). She tells me to leave while she calls the police and she will call me and tell when to come back. I left and returned when I got the call, Escalade following me all the way back. After three hours it was determined by the local police I could not take the transported to be…which was fine by me. I hauled the 3 hour trip out of town ASAP.

    Anyway…to the email blunder. I had a co-worker that needed briefed on what happened. I retold the whole story and named every MF that messed up in prep that could have possibly got me killed, what they did wrong and what I thought of it…not censoring a thing.

    My co-worker responds “Thanks, great documentation on this!” and proceeds to CC it to everyone mentioned, all Attorneys involved…and some not involved, among others not immediately on the need to know list.

    Nothing came of it on my end because they had messed up pretty bad. Turns out I was right too because the Father mentioned above later stated that they had no intention of letting me leave Chicago.

  3. Not an e-mail blunder per se, but let me submit that the accidental phone call, like your phone is in your pocket and you’re unaware the keypad is unlocked, leading to you speed dialing and then leaving an unintended voicemail, is an equal scenario.

    I was driving to school and didn’t know my phone’s keys weren’t locked. I unwittingly pants-dialed my parents’ house and proceeded to leave an almost five minute long and surprisingly clear-sounding message on their machine of me bellowing and otherwise butchering a Counting Crows song in the car, about as loud as I could. Not the most masculine-sounding of bands to begin with, I’m most definitely NOT a good singer, and I’ll be trying to live that little tape down for many years to come.

  4. I sent a text message to the head coach of the beat I was covering for the school paper. “Be there at the 11:30 game tonight or be dead.” I had a guy with the same name, who had trouble showing up to games. The coach never mentioned it, but interviews were a little weird after that.

  5. I was a freshman in highschool when someone sent out a message to the entire school congratulating the varsity football coach a reaching a milestone, don’t really recall what it was. The Captain of the football team accidently hit reply all as opposed to just reply and proceeded to basically call the coach a hack

  6. I was working with a colleague who sent a bunch of documents to about 10 people (all outside my firm) late on a Friday afternoon, requesting them to review them and return any comments to us no later than the following Monday morning. I hit the reply button intending to joke to my colleague how she had just basically ruined the recipients’ chances of having a restful weekend.

    Instead, I accidentally hit the “reply all” button, and said: “in other words, have a nice fucking weekend!”.

    Needless to say, I’ve heard about that faux pas ever since!

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