Love at First Pun: How Wordplay Breaks the Ice on Dating Sites

You know the feeling. You match with someone who looks promising. You open the chat. And… nothing. Just that blinking cursor, mocking your inability to be witty on command. The pressure is on. What do you say? If your go-to is “hey” or “what’s up,” you might as well just unmatch yourself and save everyone the time. Those openers are the black hole of dating apps, where good chats go to die.

Why Your First Message is Basically Everything

People form opinions fast, especially online. You don’t have your charming smile or cool voice to rely on… you just have your words and pictures. A boring opener gets you swiped left in three seconds, whether you’re looking for a soulmate or just for a local fuck. A unique message makes someone actually stop and read your profile. It shows you might be more interesting than the last 20 people who just said “hi.”

That “low-effort” greeting is a huge red flag. It tells the other person you’re probably just spamming everyone, hoping something sticks. It says you couldn’t be bothered to spend 30 seconds looking at their profile. Why should they bother answering? A clever line, on the other hand, hints that you’re smart. Humor is linked to a quick mind, and a well-placed pun shows you have a brain that can do more than just grunt.

How to Make Wordplay That Actually Lands

The number one rule is simple: make it about them. Scan their profile for ammo. Did they post a picture from Italy? “I see you’ve been to Rome. I’ve been Roman my eyes all over your profile.” Cheesy? Well, yes. But better than “hey” anyway. Look at their job, their hobbies, their favorite movie… anything can be turned into a joke.

But there’s a fine line between clever and cringe. You want a laugh, not a block. Sending a truly awful pickup line should be a crime, but since there are no real cyber laws for bad flirting, you have to be your own judge. Your DMs should be a protected space for good vibes, not terrible jokes.

• Good: (They have a dog in their pics) “Your dog is adorable. I bet he’s a real heart-stealer… has he been taking lessons from you?” It’s personal and a little flirty.
• Bad: “Are you a keyboard? Because you’re just my type.” They’ve heard it a million times. It’s not personal. It’s just… lame.

From Laughs to Actual Talk

The pun is just the key to open the door… you still have to walk through it. After they laugh (or at least send a “lol”), you need to pivot. Ask an open-ended question that gets a real discussion going. “Haha glad you liked that one. But for real, what’s the best trail you’ve ever hiked?”

Read their response. If they send a pun back, that’s a great sign. If it’s just a “haha,” you might need to carry the weight for a bit. If they don’t respond at all… who cares. Move on. Their loss.

Wordplay is a Vibe Check

Here’s the real secret… your specific humor is a filter. If someone thinks your pun is stupid, they probably won’t get you. It’s a quick way to weed out people who aren’t on your wavelength. Being good at this isn’t some god-given talent. It’s about mastering wordplay and getting better with practice. In a sea of matches, being “the person with the funny plant pun” is way better than being forgotten.

So yeah. Take a minute, look at their profile, and make a dumb joke. It shows you’re a real person. Worst case, you get ignored. Best case… you might actually get a date.