I once told my dad he was being bitter about wasting his life and he shouldn't take it out on those around him and learn to deal. The why: because it's the truth.

I told someone to kill themselves.
Haven't seen them since.
Granted, I apologized, but still.

Backstory: me and my high school girlfriend broke up under less than ideal circumstances, but we still had feelings for each other, it being high school and all. About 3 months after, me and a bunch of friends were going to see a movie when one of them got sideswiped and almost killed by a guy who ran a red light. We were all standing on the street, talking to the police, freaking about about what happened (my friend was fine, after about 6 months of physical therapy). She ended up seeing my on the street and thought I was the one who got hurt and sent me this huge email about how she still had feelings for me and she didn't want to lose me. Still bitter, I responded with: "I don't care if you're dying or if I'm the last person you can ever contact. Don't talk to me, don't think about me, and do not, under any circumstance, even look at me." I still feel bad about that.

I honestly don't know/remember
I'm mean most of the time and people have it coming so
Like if someone is being a little bitch (and not even the bad one but the pathetic one) I can tell them they're about to die and their parents will thank God for it and don't feel a thing

@pripyatplatypus 1) one hell of a username lol 2) that reminded me one time I sent my ex the lyrics to "puke" by eminem and they didn't realize it was a song. That was a shitstorm.

This is definitely not the cruelest thing I've ever said, but it's close and recent.
There were some boys annoying me, so I turned around and noted that I knew one of them.
They kept jostling me until I whipped around and said "You know, your sister wouldn't be proud of you." That shut him up. He's a big brother.

Not me, but my eldest sister said "It's about time that cancer gets her". About our mother. Reason : She's a bitch. No seriously, she always overdramatizes everything and the two of them did not get along that well at the time.
Personnally I always weigh my words so as to avoid saying anything mean because I hate hurting people or seeing people sad but sometimes when someone annoys me I briefly think of cruel things and last one was "get over yourself, you're his cumrug and he just needs to have a girlfriend because he's so afraid of being lonely and doesn't know how to define himself when he's alone". But that was stupidly mean to them both and totally uncalled for, it was just a passing thought that I would never have spoken aloud. (reason : she was talking when I was trying to read. + it's true, I know he was chasing someone else and settled and I know why because we talked about existential crisis, loneliness etc.)

101/10 totally gonna use "cumrug".

Cruelest thing I said was in junior high when a guy (I didn't even know him, he was a friend of a friend) wanted to take me to a dance as his friend, and I was cool with that, but then he broke up with his gf and got serious about me and I freaked out and gave him a letter that started with the classic "Close your eyes. What do you see? Nothing? That's our future" and I guess he cried when he read it. Reason: I wanted to make sure he got the point and definitely didn't have feelings for me after, cause I was a very scared little girl who didn't even want to think about being in a relationship but didn't have the heart to say it face to face. I know now that it was a bitch move and I feel terrible, but it would be so awkward to apologize this far in the future...

Let's go back a few years. I was with my (now ex) girlfriend for a total of four years. It was going well, but over time I kept noticing odd things going on such as her having to leave abruptly after checking her phone, being distant, etc. I came to learn that in the time we were together, she cheated on me with a grand total of 9 of her guy 'friends'. I lost my shit on her and left. About 2 weeks later she called and told me she was going to shoot herself in the head. I told her "Knowing how small your brain is, you'd probably miss it." and hung up. Haven't heard from her since.

Guy friend asked me out, told him I had standards...

I was passing out cake to my three friends and then my teacher. A girl said that she should get some because her birthday is on Sunday and then asked why she couldn't have any.
I said that it was for my friends.
Class rioted.

I was young, and dumb, and without even knowing what a slut was, I called my sister that. I was like eleven and she was four years younger. My mother was in earshot (Easy to achieve, when you shout the word "slut" like a bellowing bronco), and I quickly learned to google and check what words meant before tossing them around like confetti.

A friend I was very close to was being used and constantly guilt tripped by the guy she was dating... when she finally broke up with him he decided it was my fault. I politely offered to purchase a pocket p*ssy for him so he could go f*ck himself...

@tarotnathers13th it's nice seeing one that isn't about an ex... and also funny; calling a 7 year old girl a slut lmfao

So dumb, and so shameful. I look back on that with such regret for being so stupid at tossing a word I had no knowledge about as an insult. Although funnily enough neither of us knew what a slut was. One thing that did make her cry, was when we were having a fight, about 2 years earlier, I said she didn't deserve any descendants. She went crying to our mother, and my mom started berating me, but burst out laughing when she realized the reason she was crying was because my sister didn't know what descendants were and I refused to tell her.

She beated your ass before even knowing why she was crying??

Yeah, that's what happens when you make her only daughter out of four children at the time cry. It didn't help I was the second eldest, and the problem child.