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People's Proudest But Most Embarrassing Moment

When we achieve our goals, it's a natural human instinct to try and share our happiness with our friends and loved ones. But that's not always possible.

By Daniel Bonfiglio

Published 1 year ago in Wtf

When we achieve our goals, it's a natural human instinct to try and share our happiness with our friends and loved ones. But that's not always possible. 


For example, one woman in this collection is making a decent amount of money by selling her underwear online. Would her parents be proud of her for that? No, they probably wouldn't, but that doesn't mean she shouldn't be pleased with her side hustle. 


Here are 22 people and their proudest, but most secretive accomplishments. 

  • 1

    I was originally waitlisted for grad school. Later that same week the dean of the school gave me this overly friendly phone call to personally let me know I was admitted. At first I figured they were just really friendly.

    As it turns out, coincidentally, an executive of a large company who just happens to share my last name, though unrelated to me, made a significant donation to the school the same week I got my waitlist letter. Later I saw the donation mentioned in a newsletter. I never told anyone until after graduation. Everyone in admin was really nice to me there.

    People's Proudest But Most Embarrassing Moment

  • 2

    In 9th grade I got five people to sign over their souls to me on paper one signed with blood. I kept them in a jar until my mom found them and made me rip them up. I don't know what happens to their souls when you rip the contract, but I like to believe it is destroyed.

    People's Proudest But Most Embarrassing Moment

  • 3

    I once helped my sister find her crushe's house from a photo of his garden he posted on FB so she could stalk him.

    People's Proudest But Most Embarrassing Moment

  • 4

    In the last 9 months my pay jumped $38,000 a year. Combination of changing companies and asking for pay rises. In less than a year I have doubled my wage. I've only been in my career for three years, but I feel for the first time I deserve what I earn. I worked really hard and I don't tell anybody other than my immediate family because I don't want to seem full of myself or gloating but it's the first time I feel good at what I do.

    People's Proudest But Most Embarrassing Moment

  • 5

    I once climaxed just from kissing.

    People's Proudest But Most Embarrassing Moment

  • 6

    When I was nine, I beat Super Mario Bros. on a single life. Still haven't topped that.

    People's Proudest But Most Embarrassing Moment

  • 7

    I have no umbrellas because I keep giving them away to people I see walking in the rain without an umbrella.

    People's Proudest But Most Embarrassing Moment

  • 8

    I have a hobby of writing to serial killers in prison. Prior to his death, I wrote Richard Ramirez and he responded to me. He used really odd parchment with stick figure children and a sunshine in the corner of the page. He said he was only responding because he liked my name. I was really proud of that letter.

    People's Proudest But Most Embarrassing Moment

  • 9

    I'm responsible for saving the lives of at least five different people during some time spent as a first responder. None of my friends are aware that I was a first responder at all. I don't tell them because I have PTSD from that time as well, and I don't want them to treat me any differently than they do now. I still stay in contact with two of the people I saved. I'm proud of them.

    People's Proudest But Most Embarrassing Moment

  • 10

    I sell my underwear online and make a pretty good payout. None of my friends know.

    People's Proudest But Most Embarrassing Moment

  • 11

    When my brother is having a hard day, I go to his tumblr and leave nice anonymous messages to cheer him up.

    People's Proudest But Most Embarrassing Moment

  • 12

    I had an email conversation with remaining members of the Heaven's Gate cult. I do actually tell close friends about it if there's nothing to talk about, but it's creepy still.

    People's Proudest But Most Embarrassing Moment

  • 13

    I have 12 level 110 characters in WoW. All of them over 900 ilvl.

    People's Proudest But Most Embarrassing Moment

  • 14

    I am proud of getting off at the right bus stop or subway station because for some reason I have panic attacks in them, and it makes me want to just run for my life.

    People's Proudest But Most Embarrassing Moment

  • 15

    How many fanfics I write. I probably also will not tell my extended family I'm writing a novel until it is fully written and in the beta test phases. I'm honestly very proud of my work and the following my work has. People have made fanart, my bestie made an animatic for one, and one of my fics has over 100 followers, over 100 reviews and over 100 favorites. That's so huge to me.

    People's Proudest But Most Embarrassing Moment

  • 16

    I embezzled around 10k from the company where my boss was harassing me. It was HIS company of course. I couldn't have cared less about the harassment, it was almost like a pity that I let him get away with it, but he paid for it. I was 20 then, I'm 48 now.

    People's Proudest But Most Embarrassing Moment

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