Confession Time! What’s The Worst Thing You’ve Ever Done?

Readers! I’m putting together the next episode of The Jacke Wilson Show and I could use your help thinking through some issues.

Let me know (email or comments) your answers to the following:

  1. What’s the worst thing you’ve ever done?
  2. How often do you think about it?
  3. Why was it the worst?
  4. Why do you think about it as often (or as little) as you do?

Got it? That’s it! I’ll keep everything anonymous.

I have a special corollary question:

  1. Is there some small bad thing that you’ve done that you think about way too much?
  2. What is it?
  3. Why do you think it sticks in your mind?

Feel free to answer some or all of the above questions – or craft a response that has nothing to do with any of them. No pressure to follow rules! Just let me know what you’re thinking! Pour your heart out on the page!

14 thoughts on “Confession Time! What’s The Worst Thing You’ve Ever Done?

  1. The worst thing I’ve ever done? I let myself in to a friend’s store after hours. Basically I broke in. I set the alarm off and both she and the police came. At least I didn’t run. Maybe what I did do was worse. I stood there calmly and innocently and I lied. I told her I had come to clean the store as a surprise. I had not known about the after-hours alarm. I had actually gone there with a guy who ran away when we heard the sirens. I’d thought the store would be a quiet place to make out.

    I believe this is the worse thing I’ve done (it might not be), because I lied to a friend who trusted me. I worked for her, and I suppose I had always been sincere and trustworthy. I don’t think she believed I could endanger her property knowingly and lie about it.

    That’s the worse thing, to have had someone’s trust and taken advantage of them. It would be one thing if I’d told the truth, given her the choice of filing charges or not. Asked for her forgiveness. Lying was what I had been brought up NEVER to do. I was the one kid in third grade to admit to talking when the teacher came back into the room. I was the secretary who wouldn’t sign for the boss, or say he was out when he was in.

    I remember the incident of breaking into the store because I am still incredulous that I lied to someone who trusted me — as if it were the most natural thing to do. In one moment, all my moral scruples flew out the open door, I said what came to mind in order to NOT be seen for who I truly was: a young woman who would lie to avoid the shame of being arrested for such a stupid act.

    I’m thankful, of course, that my friend actually believed my lie — or decided to give me the benefit of any doubt she may have had. I don’t believe I’ve ever told anyone, and I’m surprised I’m confessing to Jack!

    I suppose the moral of my “short ” story is — you never know for sure how you will act, until you do.


    1. Wow, what an amazing story. This gave me chills. Your description of what happened – and your adult understanding of what it meant – are extremely compelling. Thank you for passing it along!


  2. The worst thing I’ve ever done, I’m not sure it’s the worst, but it is something I often reflect back too…

    I was in a serious relationship for over a year when my significant other had to move across the county due to a family emergency. They didn’t know anyone there aside from family and decided to use social media to reach out. By social media I mean they created a dating profile but insisted it was just for meeting new people and nothing else. Me, half way across the county alone and feeling insecure decided to test this idea of befriending on a social network. I created a fake account (using pictures I found online) and befriend my “significant other” and by befriended, I mean seduced. They didn’t give in, though their conversation was definitely questionable. I stopped going on the site after a few months, it became difficult to balance as my partner often talked about their “new friend” and the guilt because overwhelming as I realized they really did have pure intentions.

    I think about this often because it refers to a state of mind I never want to find myself in again. The amount of insecurity I possessed at the time is sickening and the things I did because of the insecurities is inexcusable.

    Incase you’re wondering, at some point I did tell my significant other that I was in fact, their long lost friend. It didn’t go over to well…


  3. I think any a regret would be one that has life altering consequences. I have that “girl who got away” one. Everything was great between us. I left her to move back to my old state/home when my career plans weren’t panning out. I think about it frequently. (Every couple of months). Not obsessively….just pops into my mind.
    Here was a perfect girl and I just up and left. (I was 20…and not a smart 20)
    I think about the life that could have been. Even though I am in a great marriage (25 years later). I still think about how badly I dropped that proverbial ball. I always try to make sure my selfish impulses do not affect others ever again.


  4. When I was ten or eleven, I accidentally left the store without paying for the pack of 25-cent gum I had been carrying around the store while my family shopped. When I realized I walked out of it in my hand I went back in and paid for it with my allowance money. Yes, I’m evil. *laugh*


  5. Wow. Your question makes me wonder whether I’m a sociopath because I can’t even think about ever having done anything “bad.”

    It’s either that or I’m the living, breathing definition of “prude.”


    1. Hmmm… must be room to explore this further. One of the common themes is “that isn’t who I thought I was.” Was there a bad thing someone else did that you can’t stop thinking about, because it surprised you so much?


  6. You know, now that I think about it a little more, there are a few little things I’ve done that haunt me more than they should. But I don’t label them as “bad,” I label them as “embarrassing.” I have – had, is probably more like it – a gift for putting my foot in my mouth, and when I was younger I would impulsively make really terrible and inappropriate jokes that would hurt people’s feelings.

    Occasionally these events pop into my head, and I shudder and shake them off.

    As for bad things that people have done to me, I can think of a handful of past instances where men have betrayed my trust (aka, “turned out to be different than I thought”). Cheating, not calling when they said they would, using me (this happened a lot when I was in my twenties, but it was usually on me, really), that kind of thing.

    When I was younger I would think about these things as lot. I’d remember the guy who used me to get a job, or the guy who told me he really liked me and then immediately started dating someone else, and I’d get angry all over again.

    As I’ve gotten older I tend to: a) Not be surprised as easily. We all have a little “bad” in us and it would be naive to think the people we hold dear are any different, and b) Let things go a lot more easily than I used to. The “bad” things that people do to us are usually more about them and whatever turmoil they’ve gone through/are going through, and less about us. It’s not personal, so I try not to dwell on it.


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