how to make the first move

How to make the first move


Since I’ve received so many requests on this particular topic, from both my fellow male friends and readers, I’ve decided to approach the how to make the first move and ask a woman out subject, exposing a madame’s wishes within the reality of our social channel powered lives and of course, the boring real side of it as well.

This is why I’ll tap into how to approach a woman live, at a bar/club, in public and also, how to start a conversation & break the ice on social media since dating apps & social media have drastically changed our behavior are such a big part of our nature. If you think about it, before your hormones kick in, and you start thinking if you like that person or not, your finger already knows in what direction to take the conversation.

So, whether you’re an old-school type of guy or you have embraced the swiping trend, you’ll  at least have a starting point in the last unrevealed mystery of the century: how to properly make the first move & approach a woman in order to stand a chance and not come off as a creep.


Notice that I am only using the term “woman” because the following info is not related to girls, wannabe princesses and pouting seekers of attention, mainly because I wouldn’t know what advice to offer in those cases and it’s not much a chase there, is it?

I am exclusively referring to women that know what they want, that are a presence and naturally have your attention without fighting for it, that know the difference between sexy and trashy, that you can bring to your parents, your office party and more. The sexy, smart, independent ladies – yup, that is right, the scary, unapproachable type!

Playing hard to get…with a stranger

Correct me if I am wrong, but usually, the scenario goes like this: you see her at the bar/table, with her girlfriends, having a good time.

If this is the case, be very careful with how you elaborate your moves, since if there is one thing you should know from the start is this: if she is on a girls night out, you are probably interfering with her fun and mojo, and your mere presence, will piss her & her girls off.

I know all the music videos paint a very different picture, but the truth is that girls just wanna have fun amongst themselves! You probably think they dressed up for you and other men, dancing like college girls to draw your attention and playing hard to get when not responding to your moves. Wrong!

Women dress up for themselves and/or other women, they dance with each other because it’s more fun than dancing with a guy will ever be, they are performing the song, since they know all the lyrics and hand gestures because of all the rehearsing in the car/shower and there is no such thing as playing hard to get with a total stranger that in 8 out of 10 cases just wants to be in the dance sandwich.

What you need to know about any Girls night out

Here is a basic game plan that will help you tackle any girl night out:

1. They are there for a reason: the girls have a good reason for seeing each other on that night (celebrating an achievement, a divorce, a promotion, a new haircut, getting over a heartache, getting together while one of them is in town for a few days, and so on – there really isn’t a need for a reason, but women are very busy humans, with a lot on their plate and thus they embrace a worthy reason for leaving their hair down, having a break from it all and doing something extra for them and their girls).

2. You are standing in way of that reason: this being said, you are clearly interrupting something when approaching the girl squad and it will not be appreciated. Nobody really cares that you think one of them is hot or even your potential soul mate, it’s not about you.

3. They are there to have fun together: to talk, drink, dance with one another. So, you can see now that you sending over a drink, does not mean much.

4. You are not the first and only guy thinking about hitting on one of them. Since we have established that we are talking about the kind of women that most would fancy, trust me when I say that sending a cocktail or saying you find her outfit nice will not impress her.

Now that you know you are a nuisance and you will be starting off on the wrong foot whatever you do, let’s get talking about what you could do right from there on and how to shift this into your advantage.

Pay attention

This will be a game changer, so do it properly: take your eyes out of her cleavage, the stick out of your own ego and start noticing details, like it’s the world series.

Try to figure out what the reason is, why are they out in the first place. Is it a birthday, a bachelorette party, a reunion of some kind? Tip: girls love to make it special, dress up & have props so it will be easy to see who is the birthday girl or what type of celebration it is.

How to use this info: if you like the bday gal, you have it easy. You still have to make it special in order to stand out, but you have your entry: it’s her bday.

What to do: everybody else is going to offer her a drink, right? So this is why you’ll have to do something differently. Send water to the table, if you notice the girls have only cocktails there & do it with a twist. Talk to one of the bartenders and try to get a pen to leave her a note. Say something cute, like: “To make your next morning as good as tonight! Happy Bday! From …name.” She’ll know that you have noticed it’s her bday, and you went the extra mile to make sure she will not have a killer hangover tomorrow, it shows you care.

If the it girl is not the apple of your eye, you still have to play the thoughtful card. Tip: every woman hates a guy who is rude, or simply ignoring her friend while hitting on her. You will not stand a chance if you’re doing this. Try to include her friend in the conversation, be polite, be funny and make sure you take this into consideration next time you just wanna cut into the conversation and turn your back on her friend.

What to do: same thing as above – make her aware of the fact that you have noticed the celebration and respect it all together. If you want grand gestures, champaign will work, as long you have a personal touch to it: “Making sure the celebration is as special as the person/ as your friendship”, and then go ahead and approach her saying they should add some water to the drinking menu, and you will gladly help them with that.

Whatever you do, just make it funny & thoughtful. Offer a coat, a seat, some space at the bar so she could order, while making her laugh with a clever remark. “Teach” her to order, if she is having trouble getting her order across, make it like a game, point out something that she was not aware of until now (since you were paying attention until now, you can anticipate her next moves and be there to help out). Maybe she is struggling to make herself heard across the bar, and I am sure you can come up with a funny reason for that. Tell her that you know that this is a common situation, throw some numbers (78% of women feel like that are not listen to, lucky for you I am a good listener and I also know the bartender too), make it funny.

Compliments on her outfit

I’ve had men coming up to me and saying they absolutely love my dress and couldn’t stop looking at me since I came in. Of course, I was wearing trousers at that time!

The only lesson to learn here is to make sure you know what you’re saying. You don’t have to be a fashion designer to know what you like in an outfit, yet try not to be very obvious and compliment her on her cleavage. Find something that you particularly like very much and focus on that. One of my all-time favorite compliments was related to my sneakers, a guy said he saw them first, and then the entire perfect package, and it worked like a charm. Of course, he was wrong about the brand, but it got me talking!

What to do: Pick a detail, tell her about that, choose a piece of jewelry, ask about her charm bracelet, just find a special thing about her outfit and go for it. Don’t go around saying she’s a fox, it won’t help much.

Knight in shining armor

Yes, gentlemen, this is never out of style. If you see the chance to help her out, in any way, letting her have your cab, lending a hand with her car, whatever it might be, don’t let it go by. Maybe another guy is trying to hit on her and you can save the day, Will Smith style by going over and saying: “Hi, honey, sorry I’m late” if the situation calls for your intervention. Make that your entry line and start talking about others that are trying to get to her, but clearly are doing it wrong: some may be trying too hard, some mistake her for mom and you should definitely steer clear of mama’s boys, etc.. Add humor to that and you are onto something.

You might hear the “independent woman, don’t need your help” speech, so try to reassure her that you know that fact about her, it shows and you like it. You’re just there to lend a hand, even superheroes need a break for once in awhile, right?

Online dating saga

Everything I said above about compliments, being captain obvious, and you not being the only guy who likes her, still applies in the online dating world as well.

If you already know her somehow, it should be easier to start a conversation, especially if you have common friends, events and so on. Say it was nice to see her at x event, y’s bday and that she is still the life of every party.  Say that you are sorry your profile or mind-reading powers are not working well enough for you to know where she’s going to be next, but you’re wondering if it could be the coffee shop downtown?

Pay attention – this works here as well, whether you know her or not. Look at her profile, you will easily know about her hobbies, her life, interests, books, likes, her whereabouts – that you will not use for stalking purposes, right? You can have an entry line using any of them. Is she into Game of Thrones? Tell her that you are sending over a raven every day until si goes out with you.

Don’t be afraid to be put yourself out there and be a bit quirky if that is your personality, just play along using your strengths, and let her in on some of them. If she is really great and you are dying to meet her, you could say something along the way of: “I am not even sure you are real, you can’t possibly look like that and be into star wars”.

Think of online as if everything is already in your advantage: you have the extra info on her profile, you will not be that nervous when talking to her, there is no extra pressure in this first part of you getting to know each other.

Keep an eye on your grammar, since there is no tone when messaging or texting, she doesn’t know you that well yet, writing is all you have. Be polite, funny and make sure you continue the subjects that she is opening.

Make it intriguing! Nobody actually wants to start talking to complete stranger, she already knows that you are after a date, but if you make it interesting, chances are she’ll respond back just to find out more or to keep playing that fun question game with you. Send her a cute meme with “there are 2 types of people” and start from there. Pretend that you are in kindergarten and ask her what was her fav toy/game when she was little. Take her mind on a pleasant journey, everybody wants to talk about their childhood memories, right? Or their fav band from the 90s.

The very best way to get noticed and to make an impression is to be funny & authentic, if you make her laugh you’ll have her attention, she’ll be inclined to respond since she’s already having a good time talking to you.

Tip: don’t ask her out immediately, try talking to her for some time before, in order to build a bit of common ground for your first date, similar topics that you both might enjoy and even find out where it would be best to take her out, find out what type of person she is, what food she likes and so on. It will make things a lot easier.

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