How to Casually Flirt Without Trying Too Hard

How to Casually Flirt Without Trying Too Hard

Table of Content

Knowing how to casually flirt is a bit like eating spaghetti without getting sauce on your shirt: looks simple, but it’s a sneaky challenge.

Credits: Adam Milardovic

In case you are thinking casually flirting is all about scripted pick-up lines, you are 100% wrong. It’s about sending just enough signals to someone that you are interested in without directly saying it.

It sounds more complicated than it is, and in this guide, you will learn why.

key takeaways

  • Master authentic vibes; fake swagger is a buzzkill.
  • Digital flirt? Use humor, not creepy DMs.
  • Body language speaks louder than pick-up lines.
  • Confidence counts; hesitation hesitates results.

What is Casually Flirting?

a woman flirting with a guy on a date

Casual flirting is the art of showing interest in someone without any heavy commitments or intentions. It’s light, playful, and centered around genuine interaction, focusing on creating a connection rather than aiming for a specific outcome. 

Think of it as sparking a subtle attraction through gestures like eye contact, body language, and genuine conversation. 

Simple as that. 👌

Why Flirting Casually is Your New Superpower

Being able to flirt casually is like having a secret weapon in your dating toolkit. Not all situations require heavy, intense flirting. Sometimes, light-hearted banter can do wonders.

  • It Builds Confidence: Mastering the subtle art can give you that suave edge, making you feel like James Bond at a party.
  • First Impressions Matter: We’re all in the game of impressions, and what better way than to leave a lasting one with a touch of charm?
  • You Never Know: Maybe today’s casual flirt becomes tomorrow’s date. 🍷
  • Keeps Things Fun: Not every interaction needs to be intense. Casual flirtation keeps things buoyant.

How to Casually Flirt: The Ultimate Guide

guy talking to a girl at the bar

Casually flirting (especially if you are an introvert like me) can feel like jumping out of an airplane without a parachute.

As someone who’s been through the highs and lows of the dating scene, I’ve crafted a surefire strategy that’s both fun and authentic. 👇🏼

  • Step 1: Be yourself.
  • Step 2: Make the first move.
  • Step 3: Use Proper Body Language.
  • Step 4: Use a lot of humor.
  • Step 5: Go with the flow.
  • Step 6: Ask her out in a group if you’re too nervous.

Step 1: The Magic of Being Authentic

I know I know, this is the most cliché advice I could probably give you, but listen up for 1 second.

I’ve been around the block a few times, and if there’s one golden rule I’ve cemented in my playbook, it’s this: always be yourself. Especially when it comes to casual flirting. 

Why Being Real Matters

First and foremost, authenticity breeds trust. 

When you’re genuine, people can sense it. Here’s the kicker: people can see right through your bullshit if you pretend to be someone you are not.

I see so many guys become a whole other person when they hang out with a girl they are trying to get. Dude, you can not go from a shy introvert to faking a “macho” alpha personality. Trust me when I say, it is 100x easier to embrace who you are and learn to use it to your advantage than pretend you are someone you are not.
Founder, CEO | Menprovement

Pretending might get you a laugh or two initially, but in the long run, it’s like building a house on sand—it won’t hold up. By being genuine, you establish a connection built on trust and reality. After all, real recognition is real, isn’t it?

Finding Your Own Flirting Style

Here’s the thing: Every man’s got his own rhythm, his own style. Think of it like your personal signature in the world of flirting. Maybe it’s that twinkle in your eye contact, the way you use body language to emphasize a point, or even how you flash that warm smile of yours after some playful teasing. 

Whatever it is, FUCKING OWN IT!

For instance, there is this guy I know from high school. For some reason, he could always get away with super bolt flirting techniques.

I remember this time we were discussing having drinks that night and the teacher overhead was talking. She asked what we were talking about and the guy literally said

“I am throwing a party tonight. You can come to the after-party, I’ll leave some wine in the fridge.”

And everybody laughed.

This isn’t exactly something you would say to your high school teacher,  is it?

The point I am trying to make is that he could get away with these types of comments because that’s just his personality. I can tell you exactly what to say, and to mimic all my movements, but it wouldn’t work. Everyone is different, and you just need to find THAT which makes you special and absolutely nail it. 


I’ve always been a sucker for using humor, often narrating a funny personal anecdote. It feels natural and people love a good story. 

So, the key? 

Don’t chase trends or try to mimic someone else’s style. Instead, find what makes you genuinely interesting and double down on it. 👌🔥



The Ultimate Dating Program
  • Learn how to get women without doing pick-up.
  • Completely eliminate the fear of talking to girls.
  • From the conversation to getting numbers, dates and inviting her to your place. 😏

Step 2: Seize the Moment And Make The First Move

Making the first move can sometimes feel like defusing a bomb. You get nervous, not sure which move to make, or if you should make a move at all, and one small mistake and BOOM.

However, it is important that YOU take the initiative. Studies showed that women want a man who leads them and takes initiative. This goes all the way back to the Stone Age when women depended on men for their survival. 


Not saying that women didn’t do shitback then; recent studies actually suggest that a lot of women used to be gatherers while men were the hunters.

Tackling Those First-Move Jitters

So you’ve spotted someone you’re keen on, perhaps at the same park you jog at every evening. But those butterflies in your stomach? They’re going berserk, aren’t they?

It’s entirely normal to feel nervous; we’re hardwired to fear rejection. But the real trick? Turning that anxiety into adrenaline. 

Let me help you out with some quick confidence boosters:

  • Power Posing: Sounds funny, but stand tall, shoulders back, and maintain eye contact. Feels empowering, right?
  • Reframe the Situation: Think of it as just another fun conversation. No pressure!
  • Visualize Success: Picture a positive outcome. Ever tried it? Works wonders for me.
  • You’re Physically Attractive in Your Own Right: Forget the models and actors. You’ve got your own style and charm.

Setting the Right Tone from the Start

Now, how do you make the first move and initiate a chat without sounding like you’re reading a script? Here’s the trick: Be observant and use your surroundings.

  • Simple, Friendly Openers: A “Hey, haven’t I seen you jogging here before?” can open up many doors.
  • Use What’s Around You: Notice they have a unique bag, book, or even shoes. Compliment them genuinely and ask about it. “That’s a seriously cool tote bag! Where’d you grab it?”

Now I am a man of simplicity, so don’t overthink it. Don’t ask her about the recent geopolitical landscape we are entering and what her thoughts are about it.

“Hey, this is super random but I really like your shoes so I thought I just come over and say Hi”

“Ohh haha, thanks!”

“Where did you grab them? You must be great at spotting trends”

Simplicity dude.

Step 3: Mastering the Dance of Body Talk

a young woman blushing

Let’s chat about body language – that magical tool in our toolbox that can, believe it or not, say more than words ever could. 

If flirting was a game, consider body language the joystick. A little nudge here, a slight pivot there, and BAM, you’re in control.🕹️ 

Using Your Eyes to Speak Volumes

Eye contact is one of the most important aspects of flirting.

There’s a fine line between “intrigued” and “I might be a stalker.” Looking (without the creepy staring) showcases genuine interest. 

Here is what I need you to do:

Make eye contact with her and hold it just a second longer than you would normally do. If you find this difficult, practice it with friends or just random people you are talking to. The trick is to keep strong eye contact and let her look away first. If you look away, I suggest you break eye contact to the sides and never downwards.

Breaking eye contact by looking downward shows insecurity.

But hey, eyes can be tricky. Notice her pupils dilating, or her gaze flickering between your eyes and lips? Yep, she’s interested. But if she’s looking away often, maybe dial it back a notch…

The Power of a Subtle Touch

A reassuring pat on the back or a playful nudge can make you appear confident and genuinely interested. But, bro, this one is a slippery slope. 

In the previous example of how you cold approached a random girl jogging don’t just pad her on the back because that would be weird.

You can do it more subtly. For example, if she says;

“I got the bag from Zara, I buy almost all my clothes there”

You could say something like:

“I knew you got a great eye for fashion, I buy all my clothing from Zara too”

*High Five*

I really like the high five. It is a great way to break the touch barrier and to get her accustomed to your touch. And let’s be honest, no one is going to say no to a high five.
Founder, CEO | Menprovement

Standing and Sitting the Right Way

Your posture speaks before you do. Stand tall, shoulders relaxed – you’ll exude confidence. Don’t force it. Natural, open postures send friendly vibes. And here’s a neat trick: subtly mirror her posture. If she leans in, lean in a bit. It’s a psychological thing, creating a sense of bonding. 

For instance, if she crosses her legs while sitting, give it a beat and do the same. It’s subtle, but trust me, it’s like a secret handshake that says, “Hey, we’re on the same page.”



The Ultimate Dating Program
  • Learn how to get women without doing pick-up.
  • Completely eliminate the fear of talking to girls.
  • From the conversation to getting numbers, dates and inviting her to your place. 😏

Step 4: Use a Lot of Humor

girl laughing while reading text message

Now, I’m no Kevin Hart, but I’ve had my moments.

Once tried a joke while maintaining eye contact.

“Do you believe in love at first sight, or should I pass by again?” 

She burst into laughter, but I think it was more about my awkward execution than the joke itself. Moral of the story? Humor is gold when you’re learning how to casually flirt.


Because laughter is infectious. A good chuckle can cut the tension and create bonds.

Authentic Giggles vs. Cringe-worthy Crack-ups

There’s a world of difference between a laugh that springs from genuine amusement and one that’s a mere courtesy. The real laughs come from the heart (cheesy, I know). 

Share those hilarious tales from your adventures, like when you thought wearing socks with sandals at the same park was the ultimate style statement. 🧦🤷‍♂️ 

However, certain topics are like landmines in the flirting world.

  • Religion or political beliefs 🚫
  • Personal or family issues 🚫
  • Anything that could be perceived as body-shaming 🚫
  • Dark or overly controversial humor 🚫

Playful Teasing Without Hurting

Humor combined with teasing is the spice in your flirting game. 

Just the right amount, and you’re Gordon Ramsay in the kitchen. But too much? Disaster. 

For instance, if she says she’s a morning person, playfully say, 

“So you’re the reason the rest of us can’t find good coffee in the morning” 

While keeping eye contact.

A couple of years ago, I traveled the world and I noticed that cultural barriers are a big thing with flirting. So I suggest you steer clear of cultural jokes.
Founder, CEO | Menprovement

Usually, this is what happens when the joke has gone too far:

  • When she pulls away or seems uncomfortable.
  • If that infectious laughter turns into an awkward silence.
  • If she gives you a “not cool” look or her body language shifts

On the flip side, girls want to grab a guy’s attention (or want to flirt with a guy) they often curl their hair, laugh a lot and try to make a lot of eye contact.

Step 5: Go With The Flow Bro

I remember one time at a buddy’s party when I accidentally spilled my drink and turned it into a goofy dance move. 🕺

Yep, that’s right.

There was no planning that, and yet, from the corner of that crowded room, I noticed someone trying to stifle a giggle while holding an intense eye contact image with me. That’s the magic of being in the moment. 

It’s in these unexpected situations that your charm shines the brightest. 

But how do you master this art? 

It’s Okay to Not Plan Everything

While having a few topics in your back pocket is a good safety net, it’s also essential to let the conversation develop organically. 

Let’s be real: the best laughs, the most memorable moments, often come from unplanned detours. 

If she mentions her recent trip to Spain, instead of rushing to your next topic, explore it. 

“Spain, huh? Tapas or paella? 

Another thing you can do is make witty assumptions.

“So did you go to the tomato-throwing festival? Or are you more of a Ninja bull-dodging type of girl?”

This is just a line I made up on the spot but it is 10x more flirty and interesting than when I would ask a regular question like

“What did you do in Spain?”

The second thing I like to do is to misinterpret things. This is an extremely powerful flirting technique that can make it more interesting, sexy, or funny within a split second.

“Haha, well, I went there with my parents to visit my aunt in Barcelona so it wasn’t that adventurous, unfortunately.”

“Oh, so what you’re saying is, if it had been just you and me, we would’ve turned it into a wild Spanish adventure”

Or if you want to keep it less flirty and more witty, you could say:

“So, what you’re really saying is you and your parents had a wild rooftop party in Barcelona? Must’ve been epic!”


“Aha! So, ‘visiting your aunt’ is just a code for ‘went on a secret spy mission in Spain’? Always knew you had that adventurous vibe…”

This requires some practice, but eventually, you will get the hang of it. The trick is to not put the girl on a paddlestone and just say whatever stupid, witty thought comes into your mind.

Listen More, Talk Less

So now that you have definitely sparked her interest, how do you keep the convo flowing?

Active listening. 

This isn’t about just hearing words, but genuinely picking up on her emotions and responses. If she lights up talking about her dog, dive deeper into it. 

Ask about the dog’s quirks or favorite toys. If she seems less enthusiastic about her office job, maybe steer clear and pivot to weekend plans or favorite getaways. This strategy is your golden ticket to keeping things engaging.

By adjusting your questions and topics based on her reactions, you’ll find that the chat moves fluidly, almost like a well-choreographed dance. 

Step 6: Nervous? Go for a Group Date!

a funny guy at the bar talking to a group of women

Back to that cute girl in the park. Instead of going all James Bond and approaching her solo, I thought of a more casual and less nerve-wracking way. Group hangouts. 

Less pressure, more fun, and a brilliant way to see if she’s someone you’d vibe with. 🤷‍♂️🍻

With a group, there’s a less direct spotlight on you, which means those dreaded silences or the fear of coming off as overly enthusiastic are minimized. 

How to Invite Without Pressure

So here’s how you pivot: instead of hitting her with the cliché 

“Fancy a coffee sometime?”

Try something fresh, like

“I and a few mates are having a party this weekend, you and your friends should definitely come” 

or from the example of the girl who went to Spain:

“We’re hitting up this cool rooftop bar on Friday. I heard they had great Sangria, you should come.” 🍹 

I like to frame statements as questions. So instead of “Would you like to come?” I just say “You should come.” This kind of ties back to the first part, where I talk about being a leader and taking initiative.

Pro Tip:

Choose friends who are fun and chilled. Leave that one overly dramatic friend for another day. This is a top-tier flirting strategy – a casual invite now can easily lead to a solo date later.

Cheers to that! 🍻

Bonus: Flirting in the Virtual World

blonde woman reading text message

Online dating isn’t just sliding into someone’s DMs with a “hey.” This might work with cold approaches because most guys are too shy to even try it but online… If she’s hot, she will probably get a couple of those per day.

It’s a whole different ballgame.

While the age-old techniques of eye contact and body language are fantastic for a chat at the local pub, the online world is about wit, timing, and paying attention to cues you get in texts and pictures.

But don’t worry—once you master the online playground, you’ll be able to spot a genuinely interested person from a mile away.



The Ultimate Dating Program
  • Learn how to get women without doing pick-up.
  • Completely eliminate the fear of talking to girls.
  • From the conversation to getting numbers, dates and inviting her to your place. 😏

Social Media vs. Dating Apps

social media vs dating apps

Now, here’s the thing: social media and dating apps?

They’re like comparing apples and oranges 🍎🍊. 

While both are tasty, they serve different purposes. Social media is more casual and aims to connect with friends and share cat videos.

Credits: SRHfunnycats111

But dating apps?

They’re the singles’ playground. Your approach needs to match the platform’s vibe.

Instagram and WhatsApp Mastery

DMs on Instagram and messages on WhatsApp are basically our modern love letters. Remember: these platforms are text-heavy.

You’ve got to be playful with your words, a bit teasing, and always maintain that balance between being interested without coming off too strong.

The Snapchat Game

Now, Snapchat is the wild west. 

It’s less about what you say and more about the pics you send. It’s a game of show and not just tell. It’s good to share bits of your day and make her imagine what a cool dude with an interesting life you are.

Tinder and Bumble Tactics

Both of these apps have their own vibe.

Tinder’s got that laid-back, casual feel. Great for one-night stands and quick hook-ups. On Bumble, where the ladies make the first move, it’s a bit more “serious”, or at least that’s what the users believe.

Online Dating: Dos and Don’ts

Now I don’t care if you are doing the social media slide in the DM’s approach or the old-school Tinder thing. There are some ground rules you want to follow:

  • Do: Kick things off with a light, funny, goofy opener.
  • Don’t: EVER, and I mean EVER, send unsolicited pics of your junk. It’s not a good look, mate.
  • Do: Keep the convo flowing, ask about her day, and her interests, and let her talk about herself.
  • Don’t: Bombard her with messages or display any sign of being needy. Remember, YOU are the catch, and there’s no need to rush.

Crafting the Perfect Online Dating Profile

online dating profile

Ever seen someone at a party in the corner, leaning against the wall with crossed arms and closed body language, and thought, “Man, that guy must feel awkward”? 

Well, think of your profile picture as the digital equivalent of your body language at that party.

According to a research study by Dr. Jess Carbino (Tinder’s Sociologist), people wearing glasses in a profile picture were less likely to get a right swipe. Now, I love a good pair of specs as much as the next guy, but if you’re looking to make a first impression, it’s better to flaunt those eyes.

Pictures that will skyrocket those likes:

  • Solo Shots with a Genuine Smile: Nothing radiates confidence and warmth like a genuine smile. Plus, it subtly says, “I’m fun and friendly!”
  • Action Shots: Doing what you love, be it surfing, hiking, or playing the guitar.
  • Travel Pictures: But not every picture, guys. One Eiffel Tower is enough, trust me.
  • No Shirtless Gym Selfies: It’s a no-go, fellas unless you want to attract an overly enthusiastic gym junkie.
  • Solo vs. Group Shots: One or two group shots are great – they show you have friends (which is always a plus). But don’t let your profile become a ‘Where’s Waldo’ game.

Bio: Balancing Mystery with Information

Your bio is your chance to give them a taste of who you are without handing them your autobiography. A sprinkle of humor, a dash of interest, and voilà. You’re more than just a pretty face.

Pro Tip:

Open-ended questions or quirky facts can serve as excellent conversation starters. For example, “I’ve tried and failed at learning to juggle 5 times. Got any quirky talents?”

Starting the Conversation

girl reading text message

Your first message shouldn’t sound like you’ve copy-pasted it to 50 other matches. Using details from their profile shows genuine interest. Instead of “Hey!”, try, 

“Swiped right for the cute [attribute]”

Try to find something in her picture that you can compliment on. Don’t overcomplicate it. It could be a nerdy tee, cute heels, a nice view, etc…

If you are sliding into her DM’s on Instagram and she just posted a picture of her hiking trip. I would say something like:

“Nice hiking pic Debbie, On a scale of 1-10 how epic was the view?”

Don’t be overly enthusiastic and bombard them with questions. And definitely, don’t take things too seriously. A light, fun opener like, “Pineapple on pizza – a culinary delight or a taste bud nightmare?” can work wonders. 
Founder, CEO | Menprovement

Maybe that one is a bit cliché but you get the point.

Maintaining Momentum

Remember how we discussed closed body language and feeling awkward earlier? Well, radio silence online feels just the same. 

While you don’t have to reply instantly (you’ve got a life, I get it), active engagement keeps the conversation flowing. 

And if things seem to slow down, introduce a fresh topic.

Emojis, GIFs, and Memes: Modern Flirting Tools

Smirking face emoji

You know how they say a picture is worth a thousand words? Well, an emoji might just be worth a hundred. 

These little icons aren’t just for teenagers; they’ve become a universal language. When used correctly, emojis can be the perfect way to casually flirt and set the tone for your conversations.

Let’s say you want to compliment someone’s photo. Instead of just saying “You look great,” why not throw in a 🔥 or 😍? It adds that fun, flirty twist. 

However, there’s a fine line between playful and plain creepy. So, unless you’re sure the recipient will appreciate it, maybe steer clear of the 🍑 even if she’s showing off her derriere in that latest Instagram post…

GIFs and Memes: Humor Done Right

Now we’re in my favorite territory! 

Ensure that your GIF or meme is relevant to the conversation. If she’s talking about her day at work, maybe don’t send a meme about alien invasions, unless she’s working at NASA. 

And, just like with spices in cooking, moderation is key. You don’t want to come off as trying too hard.

Keep it light, and ensure clarity. Before sending a meme or GIF, think: Will she get it? Is it universally funny, or is it more of an inside joke between you and your college buddies?

Escalating the Flirt: Signs to Proceed

So, you’ve been chatting for a while, and things are going well. But, how do you know she’s romantically interested and not just looking for a text buddy?

Here’s how you can decipher if she’s romantically interested:

  • Consistent Engagement: If she’s routinely responding, and not with just a “haha” or “lol”, that’s a great sign.
  • Personal Stories: Sharing something about her day, a childhood memory, or any related reading shows trust and a deeper connection.
  • Playful Banter: If she’s teasing you or playfully challenging you, she’s probably into the conversation.
Just ask yourself the question; How much is she invested? If you are constantly engaging and investing and get short answers back it’s not a good sign. If she’s initiating the convo and putting in effort you should move things forwards.
Founder, CEO | Menprovement

Now, to escalate WITHOUT being creepy…

  • Test the Waters with Compliments: Instead of commenting on her physical appearance, compliment her sense of humor, intelligence, or how easy she is to talk to. For example: “I always find myself smiling when chatting with you. You have such a great vibe.”
  • Progress to Voice or Video: A simple, “Hey, would you be up for a voice call sometime? I’d love to hear about [a specific topic she mentioned] in more detail,” is respectful and clear.
I am a big fan of sending voice memos. It builds trust and shows her you are a real human being and not just a psycho or something. It also shows you have confidence which is extremely attractive to females.
Founder, CEO | Menprovement

Transitioning from Online to Offline

Asian girl on date

Alright, so you’ve got the banter down, but how do you transition from pixelated flirtation to the real deal? 

It’s all about feeling the rhythm of the conversation. But let me give you a clear road map:

  • Watch for Hints: If she talks about a recent movie she watched, an art exhibit she’d love to see, or even her favorite coffee or cuisine, these are your golden tickets.
  • The Direct Approach: “I’ve been wanting to try that new Italian place downtown. We should grab dinner soon.”
  • Safety First: Always suggest a public place for the first meeting. This ensures she feels safe. 

If you are looking for a one-night stand or just something casual, you can suggest a park that just happens to be next to your place. Once you talked a bit you can suggest grabbing a drink at your place.

The day of the date

epic image of a guy texting a girl, love emojiis coming out of his phone

Communication is key on the day. Here’s your game plan:

  • Morning Message: A text that morning, something like, “Good morning! Just checking we’re still on for tonight.”
  • Plan Ahead: If you’re picking her up, confirm the time. If you’re meeting at the place, suggest a time and ask if it works for her.
  • Final Check-in: About an hour before the date, just drop a casual, “See you soon” It keeps the momentum going.
Especially with online dating, girls are more likely to bail on you since they don’t know you in real life and don’t have that feeling of responsibility compared to when they have actually met you/
Founder, CEO | Menprovement

Wrapping Up

Casually flirting is not that difficult. Make sure you go in there with a fun and positive mindset. Don’t take it too seriously, crack a joke or two, and maintain eye contact.

Misinterpretation and assumptions are powerful techniques to create a humorous, flirty vibe. If you want to learn how to date women both online and offline, sign up for the Ultimate Dating Program below. 

Currently running a free trial, so be quick before it runs out…



The Ultimate Dating Program
  • Learn how to get women without doing pick-up.
  • Completely eliminate the fear of talking to girls.
  • From the conversation to getting numbers, dates and inviting her to your place. 😏

Peace out. 


Use humor and genuine compliments, avoiding overly forward messages.

Maintain eye contact, smile genuinely, and ask open-ended questions.

Be authentic, listen actively, and relax in the conversation.

Engage in light banter, reference their profile, and avoid coming on too strong.


Our evaluations are conducted by a group of specialists based on actual experiences before they are penned down. For more information check out our editorial methodology.

Several links in this piece might be affiliated, meaning we may receive a commission at no extra charge to you if you opt fora paid service. We fully support and have personally tried these products. This website is not designed to offer financial or medical guidance. For more information we recommend reading our affiliate disclosure and privacy policy.

Table of Contents
The 6 principles of attraction by John Cooper


Learn how to NAIL the dating market and beat the competition like a pro with these simple tricks. 👇🏼

The 6 principles of attraction by John Cooper


Competition is for losers.

Learn how to get girls WITHOUT doing “pick-up” by using these simple tricks. 👇🏼