When is it the best time to introduce dark humor ino the mix?!

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Not really dark humor, but years ago I was on the phone with someone who I had just gotten to know, and I sent her the link to 2 girls 1 cup while we were on the phone. I could hear the piano music over the phone and she didn't say a word the entire time. I was just like, shit, what have I done? I thought for sure she was going to hang up on me. Then at the end she said WTF and started laughing, and re-watched it twice. We were besties for years after that.
- I asked a woman out at work. Even as I walked toward her I was thinking “this is stupid, I’m going to ruin it”.
  Then I asked if she’d ever like to catch a comedy show with me. She asked why I asked her. I said I thought she was funny. She said she’d think about it. I walked away for a few seconds, came back saying “this is stupid. This is where we work” and she agreed, saying it would go against her rules. I said “pretend I never asked”, knowing it was impossible.
  Later on we texted, and she said something like “I’m too busy for a social life (what a gentle let-down), but we can be work friends”.
  And get this … she’s actually a work friend now. We work in a big complex and cross paths sometimes, and it’s fun when we see each other. She’s funny and sweet and somehow supportive just with her presence. Like I’ll be having a rough time with a client or whatever and she’ll come by and just make eye contact and it feels like an old friend just walked in. Despite me having known her for just a couple months, she feels like an old friend.
  I dunno. I totally fucked up, broke my own rule and hers, and it still produced something valuable.
  
  That's really awesome to hear. Work friends like that make work so much better!

There's no best time. I consider instances of dark humor a Schrödinger's cat experiment.

People who can't digest dark humour and some double meaning sex jokes are not my friends. I don't have anything to do with such people.
- Not saying this is the case for you, but some people use 'dark humor' as a front for thinly veiled racism or sexism and the deliberate offense is what's not tolerated.
  
  I agree with that. But I believe that people should criticise and make fun of everything in the world to the point where people stop getting butt heart for anything and everything.

The best time was yesterday, the second best is today.
Tomorrow and every day after will also do.
- Exactly. You don't need to be popular with the majority. It's best to get to the people that "get you" as fast as possible, and not waste any time trying to "play it safe" and appeal to more people.

After your true values have been clearly demonstrated consistently for long enough that you aren't misunderstood to actually believe in the terrible thing. For example, if I make a joke about something terrible it'll be related to a subject which those close to me know I care deeply about helping.

Best is always 10 years ago. Second best is right now!

At work, news on radio was: old lady found dead in apartment, her dog had eaten her. So I said, worst part was she didn't even get to enjoy it. It did not go over well. So maybe not time is best time. But we try anyway

anytime is a good time. just rip off that band-aid and see what happens.

I relate to this so well. Touched bases with someone from high school just yesterday. Havent spoken to him in 15 years. We were talking about a good friend of both of ours who hung himself. I kept dropping comments about him "hanging around" and how he "hung out" here or there, he "knew the ropes".. but the guy never acknowledged that I was trying to make light of a heavy situation.. Or maybe he knew and wasn't on the same page. 😂
- Probably because you crossed the line from “dark” to “cruel”.
  Without speaking to him in years, and especially about that mutual friend, you have no idea how he’s viewed that loss, or has other, more recent losses that are similar.
  And you kept pushing it when he didn’t laugh, either deliberately or inadvertently using the social convention of not causing a scene/confronting someone over a joke to your advantage.
  
  mfs be like "i like dark humor aha remember our good pal we used to hangout with and love that unexpectedly hung himself aha i bet hes still hanging around... why arent you laughing... hanging in there? guys?"
  
  Thanks for the insight. Truth is I still struggle with his passing. He had a great sense of humor and we knew we could make the most dark/twisted jokes and comments to one another. I kept thinking about him when I was dropping the subtle hanging comments to this other dude. I saw it as honoring what i loved best about the deceased but maybe I'm just having a hard time coping. Thanks again.
- Or maybe he knew, but didn't want to acknowledge it because he thought it was his sick mind coming to those conclusions.
- Holy shit some people will do anything to avoid confronting difficult emotions... just say it dude
- If you make a joke that risky, and they don't laugh/acknowledge it, you really shouldn't keep telling it. They either didn't get it (and probably won't with future tellings) or they didn't like it.

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