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How To Flirt With A Stranger Like A Pro: 9 Tips

flirting with a stranger in the street

Flirting is a crucial skill to display your attraction and interest in someone. It comes naturally to some people, while others, have to work on their game.

Either way, flirting with strangers is an entirely different challenge. You’re trying to approach a person that you know nothing about.

One wrong move and he/she may start thinking of you as a creep. This is why in this article, we’re going to teach you how to flirt with a stranger like a pro.

But first, let’s talk about why flirting with a stranger is more challenging than flirting with someone you already know.


Why Is It So Hard To Flirt With Someone You Don’t Know?

Start a flirty conversation with a stranger is hard because you aren’t aware of their likes and dislikes. What turns them on, their hobbies, or anything else that you guys might have in common.

This is why starting a conversation with a friend is natural while with a stranger it’s a challenge.

And it’s even more difficult for people who already lack confidence. They feel nervous because they don’t want to look like a creep.

After all, asking one wrong question can tick him/her off and completely ruin your chances.

And in case you travel a lot, while flirting you might have language barrier problems as you see in this video…

Fortunately, there are ways to avoid embarrassment while making a flirty conversation exciting and natural. The below tips will help you with that.


9 Tips to Flirt With A Stranger Without Being Creepy


1. Connect with People Not the Internet

One of the main reasons that people lack face-to-face flirting skills nowadays is because they’re too invested in their phones.

Even when they’re sitting in a bar, they wouldn’t be aware of their surroundings.

If you also do that and then wonder “Hey, why can’t I successfully flirt with strangers?” then you now know the answer.

Most people would feel reluctant to approach you if you keep looking down at your phone. It gives the perception that you’re disinterested in talking to anyone.

So no matter where you’re, keep your phone in your pocket. Especially if you’re visiting a bar or a nightclub to flirt with strangers.

Connect with people, look around, and in general, show availability.


2. Don’t Be Pushy and Keep It Natural

The key to successfully flirting with someone you don’t know is to keep it natural but also don’t be pushy. Aggressive flirting doesn’t work with most people.

As we mentioned earlier, you don’t know what questions can tick them off, nor their temperament in general. So watch out for any signs of irritation.

Also avoid asking personal questions until he/she starts talking about them on their own. In other words, don’t be too direct with your questions.

Instead, keep the conversation general. For example, if he/she looks like a student, you could ask about what they are studying and only then ask if a hot guy/girl like them has a partner.


3. Respect Their Time and Avoid Being Clingy

There’s a thin line between flirting and being clingy. You want to avoid doing the latter.

If you’re especially flirting during the day and it’s obvious that they have to go for their shift, then respect their time. In cities like London, New York, and Tokyo you want to keep this in mind.

Even if he/she initially finds you interesting, they’d lose interest if you show no signs of leaving.

So you can flirt for a while and then end the conversation by saying “I gotta go now and looks like you’re also busy. Would you like to carry on at lunch tomorrow?”

There’s a high chance he/she would accept your offer. Especially if they showed an active interest in the conversation.


4. Ask Open-Ended Questions

Flirting is all about how you choose your words. So if you’re complimenting a stranger, don’t go like “Hey, you look really hot”.

That would just be awkward and make you look creepy. Ask open-ended questions and give non-generic compliments.

If they’re wearing a band shirt that you know about, you could go and say “This is such an awesome shirt! I really love this band, where did you get it from?”

And if you’re at a grocery store, you could go like “What do you plan on cooking today?”

Similarly, if it’s a bar and you see him/her sitting alone, strike up a conversation by saying “Do you often come here?” And then ask if they want to drink with you.

Just remember that before you ask a question, assess the environment. And although not a necessity, try finding things in common.


5. Look More Friendly and Approachable

There are multiple ways to make yourself look friendly and approachable.

This is to make sure that strangers don’t actually feel intimidated when you’re trying to flirt with them.

So let’s first start with the dressing. Fashionable dressing can do wonders but if it isn’t your strong point, you don’t have to go for anything too fancy.

Wear clothes according to the occasion. Like it should be obvious enough that you shouldn’t wear a formal suit if you’re going to a bar.

Denim jackets, polo, jeans, there are plenty of stylish clothing options you could choose from.

After that, don’t sit with the facial expressions like you have just killed a man and are plotting to hide his dead body.

Try wearing a smile on your face if possible. Especially, if you’re approaching a stranger to initiate a conversation.


6. Make Eye Contact and Smile

This trick is a classic and it’s both used by men and women in bars, restaurants and nightclubs to flirt.

But in particular, it can work like a charm for women as it gives the signal to men to make the first move. All you have to do is make eye contact with a stranger, smile for a second or two and look away.

Once again, this particularly works for women and it would be enough to make confident men approach you.

In that case that isn’t enough, play also with your hair. There are plenty of ways to flirt with a guy in person.


7. Make the Move and Break the ice

approach flirting with stranger

Breaking the ice is considered to be the most difficult part of flirting. This is where most guys falter.

However, we believe that people overcomplicate it for no reason. Most of them try coming up with witty one-liners that usually don’t work.

Always remember that the more you overthink, the harder it would become for you to approach someone.

One example of keeping it natural is that, if you’re in a mall and it’s a sunny day outside, you could say, “Damn, the weather’s so hot today!”

Similarly, if you’re in a busy district during lunchtime, you could go like “Hey, I often see you around in this area, do you perhaps work in “X” company?”

You could name a nearby company or simply make a random wild guess. It would get the conversation going.

Depending on their response, you could flirt with the other person by making funny remarks.


8. Observe The Body Language

If you’re flirting with a stranger and they keep looking elsewhere then it’s clear they want you to go.

Similarly, if you’re the only one talking and they’re answering with a yes and a no, then again, they aren’t interested.

What you want is for them to be invested in the conversation. If he/she is locking eyes with you, smiling, and also asking open-ended questions, then that’s certainly a sign of interest.

The body language of a person is enough to tell whether you should stick around or not.


9. End the Conversation by Exchanging Digits

Exchanging digits is another way to wrap things up. Especially, if you have been talking to someone for a while, and you aren’t sure if you’d see them again.

You could go ahead and say that “It was really fun talking to you! Could I get your number so we could catch up more later?”

This also opens the possibility of flirting sexually over text which helps to speed up things forward a hookup.

But in general, whenever you’re flirting with a stranger, learn to wrap the conversation at the right time and stay natural.

So that’s all for the flirting class today. Go out there and practice until you don’t become a Pro.




  • Louise And Dan

    We are born and bred Californians who love socializing, adventures, and sex. Being active in the ethical non-monogamy communities here locally and online, it's only natural for us to start this site to provide a 100% honest source of information about the sexual lifestyle in some of the world’s liberated adult destinations. We spend most of our free time traveling to hook up with singles, couples, and people of all genders around the world.