Figuring Out Humor, The Hard Way
So, you’re thinking about telling dirty jokes to her, huh? Yeah, I went down that road. Thought it would be easy, you know? Spice things up, get a laugh. Sounds simple on paper.

First off, I tried remembering some classics. The kind of stuff you hear around. Some landed okay, kinda weak smiles. Others? Crickets. Absolutely nothing. Then I thought, maybe I gotta tailor it, right? Make it specific. So I spent some time trying to figure out her kind of humor first. Watched what shows she laughed at, listened to the kind of banter she had with friends.
Here’s what I kinda found out through trial and error:
- Timing is everything. Like, absolutely everything. Telling one at the wrong moment is worse than telling a bad joke.
- It’s gotta feel natural, not forced like you memorized it from somewhere five minutes ago.
- Knowing her boundaries is key. What’s funny to one person is just plain gross or offensive to another.
Honestly, the whole “dirty joke” thing can be a minefield. You think you’re being charming and witty, but it can backfire spectacularly. Which reminds me of this one time, completely different situation, but taught me a lot about trying too hard to be clever.
I was trying to impress this girl, years back. Not with dirty jokes, but with what I thought was sophisticated wit. We were at this kinda fancy dinner thing for a mutual friend. I was dropping these observations I thought were really smart, kinda edgy maybe. You know, trying to sound like I knew stuff.
Turns out, I just sounded like an idiot. She was polite, but you could see her eyes glazing over. Later, her friend kinda pulled me aside and basically said, “Dude, just be normal. Talk with her, not at her.” Hit me like a ton of bricks. I was so focused on performing, on trying to be this “funny, smart guy,” that I forgot to actually connect.

It wasn’t about the specific jokes or witty lines. It was about the pressure I put on the situation, trying to force a certain reaction. And that’s kinda how I feel about the whole “dirty jokes for her” mission sometimes. If it happens naturally in conversation, great. But setting out specifically to “deploy” dirty jokes? It often feels awkward and performative, just like I was at that dinner party.
So yeah, my practice now? Less about finding the “perfect” dirty joke and more about just vibing, seeing where the conversation goes. If a moment for some edgy humor comes up naturally, cool. If not, also cool. Less pressure, way better results. Learned that the hard way, not just with jokes, but with trying to be someone I wasn’t at a dinner table.