How To Start A Conversation With A Random Girl

by Andreas | Last Updated: September 14, 2019
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If you’ve never been called a creep for how you approached some random girl on the subway or at the bar, then you must be one lucky human! The rest of us have had our unfair share of miscommunication, we’ve come off too sleazy, and we’ve had to reconsider the art of talking to random girls.

But to tell you the truth, starting and holding conversations with random girls is never that easy! And it’s harder when you are trying really hard to hide your ugly and unaccomplished behind the masculine veneer of perfection. 

And to be honest, approaching and striking up a conversation with a random attractive girl is one of those things that most of us would rather not do because: why bother when you don’t even know the first thing you should say? 

Having had sad conversations flops, some which ended in me not walking around some streets for months and others that have resulted in great friendships spanning years, I believe that I know a thing or two about starting (and holding) actual conversations with random girls.

So, let’s end all that awkwardness right here, right now! 

In this piece, I share insights into how to hold smooth conversations with a random girl. Out of the excitement, you might end up saying a thing or two you didn’t mean to, later regret, or even wish you’d said something else, but at the end of the day, you will hold a conversation without stuttering or sweating!

#1. Shift your Attitude

What creates that sleaziness in men approaching random girls comes down to the simple fact – that this guy wants that girl, more than she does. This attitude will automatically force you to place the lady high up on a pedestal.

Once you do this, you lose it because you don’t really know how to react to or talk to this attractive queen whose throne you just stepped on (yeah, I’m definitely overly dramatic, but you get the point).

To downplay the tricks, your mind is playing on you, try a different approach. For example: Yes, she’s hot with the most beautiful eyes you’ve ever seen, but that can’t be the only thing going for her. Is her life interesting and fun? Is she caring? What does she think of Brexit? 

With such thoughts, your mind will automatically switch from talking to a goddess in front of you to a beautiful girl who might be fun to hang around. 

Also, once you’ve lowered her from that pedestal, there’s an instant powerplay shift where you become the selective, confident, high-value gentleman.

#2. Self-Awareness in Body Language

 Body Language

Do you know what makes you creepy, even when you approach a girl with the best intentions? Not being aware of your body’s reaction as you talk to her.

We are talking about trying hard to maintain eye contact only to end up staring at her, WITHOUT blinking! Man, that’s creepy! 

You need to avoid this staring contest mistake. And you can do it by making just the right level of eye contact. 

Don’t leer at her. Don’t focus on a specific area or part of her body with that intense, hard, and unblinking stare.

Instead of these creepy-looks, make her attracted to you instantly with soft and relaxed gazes. The best thing about the soft gazes is that they make it easier for you to take more of her beauty and elegance in; even without her knowing.

Also, there’s something magical I learned from my grandfather – the art of smiling with the eyes. Yes, it’s an art. You have to remember and master that warm feeling that you have in your eyes after a burst of hard laughter. This laughter is real magic; it oozes warmth and friendliness.

Now that we’ve covered eye contact let’s go down to your shoulders. Once you’ve decided to approach her, keep your shoulders back, the back straight, head held up high, and smile.

#3. What to say

Now that you have her attention and you look like a very high-value man, you need to make sure that you actually get the words out, right. 

Rule 1 – Compliment her

You’ve obviously been checking her out for some time. What’s the one endearing thing that you just love about her and how she looks? Tell her, you like it. No backstories. No explanations. But be genuine about the compliment you are giving her. Say it as you mean it.

Compliment her style, jacket, hair, or eyes. And when you choose to tell her just how gorgeous her eyes are, you better do it with enough excitement and enthusiasm.

Rule 2 – Never Use Pick Up Lines

Unless you can recover from an eye roll masterfully and still keep her interested in the convo, or your pickup line is super hilarious, steer clear of pickup lines. Pickup lines are corny with a 90% chance of success.

So, if you like your chances with the girl, stick to the genuine compliment, mean what you say and smile. Remember that she will see right through any and all disingenuous compliments.

Phone Anxiety can cause many problems and guys might never get the girl of their dreams…

Rule 3 – Show Interest

Get the ball rolling with some playful banter to create that safe and relaxed environment for you to hold a conversation. 

You could ask her questions about her recent adventures and even the good-old-interested-but-unsure-guy-question, ‘what do you do for fun’ or ‘what’s your deal?’ Just remember to keep the conversation light and the vibe fun. 

#4. Blame the Social Norms 

 Group Of People

For most guys, meeting a girl during the day and chatting then up is not an actual definition of normal. It is, in fact, very awkward. But you don’t have to pass up that opportunity.

If you wish to talk to a girl during the day and are unsure about what to say, you could start the conversation by noting that you understand how awkward that encounter is but you don’t really care.

For example, you could start off by saying, ‘I know that this will come off a little weird, but I just wanted to come over to meet you. Oh, you have the most beautiful eyes/ hair I’ve seen!’ It doesn’t have to be much; all you have to remember is to remain cool and confident. 

Check out Meet Your Sweet for more pointers in mastering self-confidence and holding down a conversation for more than 10 seconds.

#5. Be a man with integrity

Puzzle spelling trust

Do you appear different than, you claim to be? Do you stand by your opinions, thoughts, feelings, and values? Women are attracted to men who have and show integrity. 

What this means is that you should be able to share your opinion, listen to their opinions, disagree with them, and actually stick to your guns. Doing this, even when you are discussing bagels, burgers, books, or movies earns you several points from that lady. It shows that you are confident. Don’t forget to hold your ground with a smile on your face.


Your ability to start a conversion with a random girl is a lot more than saying the right things, you need to be great at conversation and that means being aware of everything from your body language and expectations to know what to say and how to say it.

Andreas, the founder of CharmingMale, is an enthusiast of becoming a "charming guy" without becoming someone else. He has been an average skinny dude most of his life, yet after years of hustle, disappointments, he become a better male version of himself. He discovered that, even if you are an average guy, as long as you are willing to put in some effort of improving yourself and developing the skills, you can become a better man that people will respect and admire!