Why Pick-Up Lines ‘Always’ Work

Oluwatobi Ajayi
4 min readNov 10, 2023
Photo by Brooke Cagle on Unsplash

If you have ever approached a stranger that you’re attracted to, you can allude to how nerve-racking the experience can be. Depending on the setting, asking someone on a date or for their number requires a combination of skills that most people haven’t mastered.

In fact, women do not know that most men are terrified of them. Psychologically speaking, men and women do not speak the same language, and neither are we the same species. So, for most men, approaching a woman is the equivalent of meeting an alien species.

You need NASA-level training, knowledge of alien tech, and intergalactic diplomacy. For better or worse, we’re stuck with them till the Asgardians join us in 2029.

Fingers crossed.

This is where pickup lines come in. Pickup lines are simply hilarious puns and corny jokes that break the ice. It is the relational equivalent of a cold-pitch. A condensed poem — if you will, like a haiku.

The question then becomes, what makes pickup lines so effective?

Here are the three reasons why pickup lines (almost) always work. They all revolve around things women instinctively find attractive in men. However, very few people can articulate the inner workings of the female mind.

So, you’re welcome.

1. Humour

As I stated in my Medium on having a successful talking stage, humour is the elixir that lubricates your way to a woman’s heart. Your typical pickup line is cheesy enough to make a woman roll her eyes but funny enough to make her smile. Like a comedic punchline, it requires a proper understanding of timing, facial expression, and reading your audience.

When delivering a pick-up line, your goal is simple. Make her smile. It softens her demeanour and brings down her guard, making her more susceptible to the rest of your speech. Sometimes, the difference between a stranger and a ‘cute’ stranger is who made her smile.

2. Confidence

While many consider pickup lines a trick that shy little guys use to hide their fear, I consider pickup lines a tool of masters. A punchline is an assertion. A definite statement that demands a response — an instant one at that.

Imagine walking up to a lady and saying, “You owe me a drink. Cos when I saw you, I dropped mine.” That’s an accusation, a funny accusation. A novice would not start with something that risky. Mastering the delivery of pickup lines requires a solid dose of confidence, which ladies love.

3. Intelligence

Punchlines are a product of wit. The good thing is that nobody cares if it’s your wit or ChatGPT. Women are generally attracted to intelligence, and a good punchline shows that you have the aptitude to understand and craft one.

The best punchlines involve a blend of wordplay, subverting expectations, and a feel-good element to it. So, with a single line, you manifest your inner Shakespeare, Trevor Noah, and Giacomo Casanova.

What a combination.

Guidelines On Pickup Lines

Now that you know how this ancient communication device works, here are two things to consider on your next pickup.

The Art of Delivery

You may have noticed one word pop up repeatedly in this writeup: Delivery.

Without proper delivery, even a great pick-up line can taste like sawdust in the mouth of your audience. Just like when your friend tries to retell a very funny joke, but you’re standing there in annoyance as they laugh hysterically.

Pickup lines are more than the lines. Pickup lines require charisma. Pointed, confident eye contact and a mischievous smile on your face to show that you’ve done this before — even if you haven’t.

Understand Context

Here are two pickup lines for your consideration:

To quote the poet Katy Perry, “You make me feel like I’m living a teenage dream.”

If you were a fruit, you’d be a fine-apple.

The first one makes a lot of assumptions. First, you must know who Katy Perry is and be conversant with her discography. Then, you must understand the cultural context of the term ’teenage dream’. That’s too many assumptions and a sure way to bomb your pickup line.

The second one, on the other hand, requires that you know about fruits. That’s it. Since pineapples are one of the most popular tropical fruits in the world, your success rate is significantly higher.

My point is, when next you’re shopping for pickup lines from Google or Kraks TV shows, employ intuition when deploying it on your target.

I believe that with this short expose, you can go into the world and sweep (almost) any woman off her feet. Cos, what’s the worst that could happen?

She’d either say yes or no

…or eww.

But that’s not going to happen. Right?

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