You're staring at your phone. The cursor is blinking like it's judging you. You want to send something that isn't just a "hey" or a boring "how’s your day," but you also don't want to come across like you're trying way too hard to be the next stand-up comedy sensation. It’s a weirdly high-pressure situation for something that’s supposed to be fun. Honestly, the secret to flirty texts to make him laugh isn't about having a Netflix special’s worth of punchlines. It’s about the "pique." It’s about catching him off guard in the middle of a mundane Tuesday.
Most people play it way too safe. They stick to the script. But if you want to actually occupy space in his head, you’ve gotta lean into the absurd. Humor is the ultimate shortcut to intimacy. A 2017 study published in the journal Evolutionary Psychology actually found that for both men and women, a sense of humor is one of the most highly valued traits in a partner. It’s not just about being funny; it’s a sign of intelligence and social "with-it-ness." When you make him laugh, you’re basically hacking his brain’s reward system. Dopamine hits. He associates that feel-good spark with your name popping up on his lock screen.
But there’s a line. Cross it, and you're just the "funny friend." Stay too far back, and you're just another contact in his phone. The sweet spot is that mix of "I’m cute" and "I’m slightly roasting you."
The anatomy of flirty texts to make him laugh
Let’s get real about why some texts land and others just die in the notifications tray. Context is everything. If he’s in a high-stakes board meeting and you send a three-paragraph joke about a penguin, it’s not going to work. Timing is your best friend.
The best flirty texts to make him laugh usually fall into a few buckets. You’ve got the "False Accusation," the "Self-Deprecating Flex," and the "Hyperbolic Demand."
Take the False Accusation. It’s a classic. Instead of saying "I miss you," which is fine but a bit standard, try something like: "I’m currently filing a police report because you’ve been living in my head rent-free for three days and it’s a blatant violation of my mental property rights." It’s ridiculous. It’s clearly a joke. But it also tells him exactly what you’re thinking without the heavy emotional weight of a "serious" confession.
Psychologically, humor acts as a "buffer." Dr. Gil Greengross, an evolutionary psychologist, has written extensively about how humor functions as a fitness indicator. By being funny, you’re showing you have the cognitive flexibility to play with language. Men, in particular, often report feeling a massive sense of relief when a woman takes the lead with humor because it lowers the "rejection anxiety" that usually plagues the early stages of dating.
Stop being so polite (it's boring)
Seriously. Stop.
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If you're constantly "just checking in," you're becoming a chore. Think about the last time a text made you kick your feet and giggle. It probably wasn't a polite inquiry about your lunch. It was probably something a bit chaotic.
Try the "Over-the-Top Review." Let's say you guys just grabbed coffee. Instead of "That was fun!", try: "Giving our date a 4/5 stars. The company was elite, but you didn't let me win at the sidewalk crack stepping game, so I’ve docked a point for your blatant lack of chivalry."
It’s a roast. Men love a gentle roast. It shows you’re confident enough to poke fun at the dynamic. It also gives him an easy "in" to defend himself. He’ll likely fire back with something about how he’s a professional athlete at sidewalk walking, and boom—you have a bit. "Bits" are the foundation of every great relationship.
The "Useless Update" strategy
Sometimes the best way to be funny is to be incredibly specific about something totally unimportant. Details are where the humor lives.
"I just saw a dog that looks exactly like your LinkedIn profile picture and honestly, I think the dog wore the tie better. No offense."
"Just so you know, I was going to be productive today, but then I remembered you exist, so now I’m just staring at a wall. Hope you’re happy with yourself."
These work because they’re low-stakes. You aren't asking for anything. You aren't demanding a deep conversation. You’re just dropping a little nugget of personality into his day. It’s the digital equivalent of a wink.
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Why "Dad Jokes" actually work in flirting
We need to talk about the "so bad it's good" category. The pun. The groan-inducer. While "Dad jokes" get a bad rap, in a flirty context, they show a lack of ego. You aren't trying to be "cool." You’re being dorky, and dorky is approachable.
If you can lean into a pun that’s related to his job or a hobby he mentioned, you’re doing two things: you’re making him laugh (or at least eye-roll), and you’re proving you actually listen to him. If he’s an architect? "I’m really 'building' up some feelings for you, but I promise the foundation is solid." Yes, it’s cringey. That’s the point. The cringe is the bridge to a real conversation.
A lot of people think they have to be "sexy" all the time to be flirty. That’s exhausting. And frankly, it’s a bit one-dimensional. Being the person who can make him snort-laugh while he’s standing in line at the grocery store is way more powerful than just being the person who sends a "hot" selfie.
Handling the "No Response" or the "Dry Response"
We’ve all been there. You send what you think is a comedic masterpiece and he replies with "lol" or, worse, nothing for six hours.
Don't panic. And for the love of all things holy, don't send a "???" text.
Humor is subjective. Maybe he’s busy. Maybe he’s not a "texter." Or maybe your joke about the sentient toaster didn't land. It happens. The beauty of using flirty texts to make him laugh is that they are inherently "disposable." If one doesn't work, you just pivot back to normal conversation later. You don't need to acknowledge the "fail." Just keep moving. The most attractive thing you can do is stay unbothered.
Using pop culture as a crutch (in a good way)
If you’re struggling to come up with original material, use what’s already out there. Memes are the universal language of the 21st century. But don't just send a random meme. Add a caption that makes it personal.
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Find a picture of a very stressed-out looking raccoon and send it with: "Live footage of me trying to decide if I should text you or stay mysterious and cool (the raccoon is winning)."
It’s self-aware. It admits you’re thinking about the "rules" of dating while simultaneously breaking them. That kind of transparency is incredibly refreshing. Most people are out here playing 4D chess, trying to figure out the exact number of minutes to wait before replying. When you just admit, "Yeah, I’m overthinking this," it’s funny because it’s true.
Practical steps to level up your texting game
Don't overthink the word count. Sometimes a two-word text is funnier than a paragraph. If he sends you a photo of his dinner, and it looks mediocre, just reply: "Prison food?"
It’s short. It’s a little mean. It’s a lot funny.
- Audit your current thread. Look at the last ten messages you sent. If they all end in a question mark or a "hope you're good," it's time to shake it up. Drop one "absurd" observation today without expecting a specific answer.
- Lean into the "We." Create a fake rivalry or a shared "enemy." If you both hate a specific popular movie or a certain type of food, use that. "I just saw someone eating Hawaiian pizza and I immediately thought of our shared trauma. Hope you're coping okay."
- The "Accidental" text. "Oh my god, I just saw the hottest guy... wait, never mind, it was just a mirror. My bad." It’s a classic for a reason. It’s silly, it’s confident, and it gives him a reason to tell you how "vain" you are, which is just another form of flirting.
- Use voice notes for comedic timing. Sometimes the "deadpan" delivery is what makes a joke work. A five-second voice note of you saying something absolutely ridiculous in a very serious voice can be 10x more effective than a text.
The goal isn't to become a different person. It’s just to let the filter drop a little bit. We spend so much time trying to look "perfect" on dating apps and social media that we forget that most people are actually just looking for someone they can be weird with.
Start small. Pick one thing that happened to you today that was mildly embarrassing. Instead of hiding it, text him about it like it’s the greatest tragedy of the century. "I just tripped up the stairs in front of a group of teenagers and I’ve decided to move to a different state. It’s been nice knowing you."
He’ll laugh. He’ll probably tell you about a time he did something stupider. And just like that, you aren't just "the girl he's talking to"—you're the person he actually wants to talk to.
Stop worrying about the "right" thing to say. The "wrong" thing is usually much funnier anyway. Focus on the vibe, keep it light, and remember that if you're laughing while you're typing it, he'll probably be laughing when he reads it. Turn off the "perfection" switch and lean into the chaos of being a human being. It’s a lot more attractive than a perfectly polished, boring text ever will be.