From Introduction to Intrigue: How to Approach and Flirt with Women

Last updated on : February 06 2023

couple flirting closely

What Is Flirting

Flirting is an art and a science. People flirt because they want to start, build, and maintain an exciting romantic connection with another, their crush.  

At its core, flirting is a light, playful stance on pushing your crush away and pulling them back in. It's a delicate balance between playfully displaying your desire and then taking it away cheekily, in a cycle that builds a robust and healthy connection. 

When done well, flirting flows both ways and fulfills our strong desire for connection and validation between couples in contact. 

You flirt by first approaching your crush and then holding a playful conversation using several different techniques, like eye contact, smiling, touching, and body language. All of which you can learn, practice, and become an expert in. 

Flirting is something you need to do throughout your relationship, not just at the start. It's core to keeping the love and attraction in couples alive, so it's a great skill to learn and maintain. 

Read more: How To Flirt With A Girl By Text

About This Guide

Start to learn how to flirt now by using this intense and detailed guide. In it, we focus on how you might approach your girl crush for the first time and then successfully flirt with her. 

We've written the guide for men wanting to approach and flirt with a female crush - a strong leadership quality in men. However, also use it if you are a man looking to improve your flirtation skills at any point in your dating or relationship cycles.  

We will follow up with a similar guide for women later.

How To Approach A Woman

girl looking to be approached

Before you start flirting, you need to assess the situation and environment and make an approach. 

Is Your Crush Approachable? 

Some people don't want you or anyone else to approach them, and you need to respect their boundaries. On the other hand, some people will find you immediately attractive and cry out for your attention. And others will be somewhere in between. 

It would be best if you learned where your crush is on this spectrum of approachability. Sometimes it's going to be noticeable. Other times you're going to get it wrong. Practice will make you perfect. 

Here are some pointers.

  • If your crush is wearing headphones or earbuds, she will not be happy to be approached. Particularly if she has her head in a book or telephone, has closed body language, a pulled down cap, and dark glasses on. 
  • On the other hand, if she is sitting alone at a bar counter, briefly making eye contact and smiling at you, it is safer to make your approach. This behavior is often an invitation to you.
  • In the middle is the crush you've seen at the gym a few times, or in your college class. You're strangers but not perfect strangers, and you're on a similar level to her. If you want to approach this crush, you need to find the right opportunity to maximize your chances of success while treating her respectfully.   

These thoughts lead nicely to our next point. 

Dealing With Proximity

To begin flirting, you need to be close enough to talk, texting is not flirting. You need to be close because the techniques you need to flirt effectively are in your conversation, your smile, your eyes, and your body language. So you have to get close enough to display these. 

Finding a way to get close enough to begin flirting can be challenging. You might need to get inventive. 

However, here are some things you mustn't do. 

  • Never approach anyone who doesn't want you to; this is the person with headphones on, the closed body language, etc. 
  • Never approach anyone from behind or surprise them. Coming to a person like this, especially a person who doesn't know you, is creepy and could get a bad reaction. 
  • Never approach anyone with a touch, unless expected to do so through a formal greeting, like a handshake. So don't tap on someone's shoulder to get the person's attention.
  • When you approach, always make sure there is plenty of room for your crush to walk away or escape your approach. You don't want to stand in front of someone in a way that might threaten them or their personal space. Flirting requires consent, so allow people to accept or reject you easily.

The Best Way To Make Your Approach

The best way to make your approach is to make eye contact and try out a smile first. If someone makes eye contact and smiles, then as we mentioned before, you are in a safer place to approach them, but still, always with the utmost respect. 

If you want to approach someone but haven't got the eye contact or smile yet, try to spend some time close to them before saying something. Often this is a good test of whether they want your approach or not. 

For instance, at the gym, use the running machine close to theirs. Or set up your training mat near their mat. If they like you close, they might smile or make an opportunity for you to speak with them. If they move away or don't notice you, then you know. 

Timing Your Approach

A few words on timing. If you're getting the eye-contact and the smile, you must nerve up and make your approach within a few minutes. Be confident and strong, or leave it too long, and you'll destroy the moment. 

Similarly, if you're putting your gym mat next to your target, do it once. Please don't do it every session for a few weeks. Again this is creepy. Do it once, assess, and then make your approach, or move on.  

If you're showing interest through your actions and not breaking the ice by making conversation, you'll come across as weird. Avoid this.  

The Opening Line

Once you've made your approach, you need an opening line. 

The best opening line is a simple opening line, one that is genuine and respectful. You don't need stock lines. Although stock lines can work, you run the risk of coming across as insincere and even untrustworthy. 

An excellent example of an opening line is introducing yourself. Or if you are a more advanced flirter to comment on the surroundings or similar, in a fun and playful way.

Although you might think so, there's not a lot of science in the opening line. You merely want to say something confidently that's polite and opens up a conversation. So don't stress too much about what you need to say. Trust yourself. It'll come to you when you need it.  

Your objective for the opening line is to break the ice, determine the level of interest in you, and set yourself up for a romantic conversation. If there's no interest, then move away and leave the person alone. If there is interest, then it's time to bring out the rest of your flirting armory. 

You will need several flirting techniques to differentiate your conversation from a friendly encounter and turn it into a boiling hot romantic interest. 

Read more: How Women Test You And How To Handle It 

How To Flirt With A Woman - The Eight Principles Of Effective Flirting 

couple talking and laughing

Here are the eight principles needed to flirt with a woman effectively. 

1. Maintain A Conversation

After the opener, you need to maintain and develop the conversation long enough to pique interest and reach your objective. Usually, this is getting a telephone number so that you can ask your crush out on a date.  

The rule of thumb is to keep the conversation light and comfortable—nothing personal, nothing heavy or negative, and nothing about your wants or needs. You're not going to be asking the woman you're talking with to be your girlfriend, for instance. Instead, ask open questions and try to get her to talk more than you. Use your wit and sarcasm to provide a humorous experience.  

Talking with someone needs to be natural, light-hearted, and enjoyable to both of you. If you're struggling to keep it honest and flowing, then maybe say thank you and move on. It might be that the chemistry is not there, and this is not the girl for you. Please don't force it. 

If it's going well, then set yourself an objective to end the conversation on a high, and ask for her telephone number. At this point, you want to remove yourself from the vicinity, leaving her happy and wondering whether you will contact her or not. 

To distinguish the conversation from a friendly chat, employ the remaining principles to clarify your romantic intentions.

2. Be Humorous

Firstly, being humorous is a large part of flirting. Flirting is light-hearted, comfortable, non-threatening, and fun, and humor supports all of these emotions. 

So in your conversation, employ your best skills at being humorous. 

But in this instance, being humorous doesn't mean being a clown or ridiculing yourself or others. It means being playful and getting your crush to laugh. If you get to the point where she is laughing, and you're leaning back with a cheeky grin, then you are flirting like a pro.

Secondly, you can use humor as a way to filter out crushes not interested in you. If they're not laughing with you, then possibly there's no chemistry, and it's time to move on. 

So yes, do use humor to make your conversation fun and sexy, and as a way of quickly deciding whether this person is worth your flirtatious investment or not.

3. Limit The Compliments 

We specifically mention compliments because so many men believe they are a necessary part of flirting. But they have hardly any importance in a flirtatious encounter.

Many women expect compliments when approached, and so compliments can be boring to a girl. Also, if done excessively, compliments come across as insincere and can make you look wanting. They also put your crush on a pedestal when she'd prefer to be your equal or to look up to you. 

So refrain from making compliments. You'll come across as different from most other men. And if you don't compliment her at all, she might find this unusual and start praising you instead.  

4. Make Effective Eye-contact

We've already discussed trying to make eye contact and getting a smile before the approach. However, while in conversation with your crush, the right type of eye-contact is hugely flirtatious. 

Mostly you want to look into her eyes and keep your gaze a little longer than you would for a friend. However, you also want to look away often. 

Use eye contact as a push-pull technique. Pull your crush in with a longing gaze combined with a naughty smile. But look away often enough, feigning disinterest to push her away. It's a delicate balance. 

When either of you is talking, it's best to keep eye contact. Then use some of the time in between talking to look away. 

A technique to understand how much interest there is in you is to stop talking at an appropriate point and look away. Allow the silence to continue and see if your girl crush reengages you. This push technique is likely to pique her interest in you.  

You can also wink or hold a gaze in silence. Do this playfully, to get your crush to laugh or smile. It must be laughter or a smile you are after with this type of eye contact. Otherwise, the interaction is too heavy at this point and can be creepy.  

5. Smile Cheekily

When flirting, you don't smile to seek approval. Instead, you smile to emphasize a point and to be naughty. 

For example, smile to let her know that you're joking when you playfully push her away. Say she asks what your type is, and she is petite with dark hair. You might say well, you prefer tall blondes, but you say this with a cheeky smile, so she knows that you are playing with her.  

Practice smiling slowly and smiling with your eyes more than your lips. It's a smirk you are after, not a vast beaming ear to ear grin. Try not to smile when you don't need to. Use it only to be naughty or emphasize a playful point. 

Lastly, holding eye contact and smiling at the same time is very sexy. It causes your eyes to wrinkle and come across as open and inviting. Try this briefly when she breaks the silence after a pause in the conversation before responding to her.  

6. Touch Appropriately

Before you touch anyone, you need their permission. However, sometimes this permission is implied or is appropriate in the circumstances.  

Know that touching is hard to get away with if you've done it wrong. So you either need to ask whether you can touch someone (which can be very flirty in itself) or you need to do it appropriately and with respect. If someone asks you to stop, then you must do so immediately. 

Generally, touching lightly on the shoulders is safe. As you move down towards the hands (and lower), the touch becomes more intimate, and of course, dangerous.

6a. How To Initiate A Touch

You might want to initiate a touch by trying to rub shoulders or arms in conversation or gently bumping into your crush and seeing what the reaction is. If the woman you're talking with doesn't resist or recoil, then you can maybe try something bolder like a touch on the shoulder, forearm, or a gentle tap on the hand.

The perfect set up for this approach is to sit side by side at a restaurant or bar. Close enough to rub shoulders or arms, or legs. Be led by her actions. If she's sitting closer to you than ordinarily necessary, she might be open to you touching her. If she's keeping a safe distance, then you know she doesn't want your close attention.   

6b. The Art Of Touching

Once you've established touching is acceptable, then the art is not to overdo it. And to do it lightly, not for long periods and in context. You don't want to grasp her hand and hang onto it, for instance - this is creepy. You also don't want to touch out of context - try a touch when you are both laughing, for example. 

Ideally, you want to touch, then remove your touch. Wait a while, then do so flirtatiously again. You'll know you're doing it right when your girl crush starts to return your contact or looks for ways to get you to touch her again.  

6c. How And When To Ask For Permission To Touch

Asking is best done when you want to kiss. Although acceptable, it's weak to ask the girl you are talking with if you can hold her hand. So if you're going to ask, go for the big one. 

When to do this? Well, it depends entirely on the chemistry between the two of you. And your courage. As long as you do it respectfully, there's no harm in asking, so practice and you'll soon work it out. 

6d. Types Of Touches

Apart from the conversational touches we describe above, you can also use your surroundings to help with touching. 

Here are some examples. 

  • When greeting, you can hold your girl crush's hand just a second longer than expected while looking her in the eyes. 
  • You can also touch her to get her attention towards an event or thing occurring near you. For example, suppose you're at a football game. In that case, you can touch her appropriately to draw her attention to something happening on the field. 
  • You can take her hand gently while leading her somewhere, across a road, for instance. 
  • You can appropriately remove something from her hair, or similar as a caring touch. 

All of these can be powerful ways to flirt if done correctly.   

7. Display The Correct Body Language

A large proportion of our communication is non-verbal - and so what we do with our bodies while flirting is essential. 

For example, arms unfolded, and your shoulders and feet facing your crush is typical open body language. And this type of body language pulls your girl crush into you. At the same time, closed body language pushes her away.

An excellent way to run with your body language is to start semi-open and then open up more as your conversation develops. This opening up rewards your crush for her interest in you and the conversation.  

A shoulder to shoulder stance can also be powerful, helping develop a strong connection between you and your crush. Think of two warriors fighting shoulder to shoulder, or two close friends walking shoulder to shoulder. 

And so we recommend shoulder to shoulder as an excellent way to commence your flirting if you can. This approach means sitting next to her at the restaurant or bar counter. Then, as the flirting intensifies, you can turn towards your crush to display more of an open body style and allow touch and kissing to happen easier. 

Lastly, observe and get feedback from your girl crush's body language. If she's displaying open body language, it likely means she's interested. Also, look out for other subtle and positive signs, like your crush playing or twirling a strand of her hair in her fingers. 

If she displays closed body language, then either you need to warm her up quickly or move on. 

8. Pull It Together With Push/Pull Techniques

Flirting is a dance around the perfect balance of pushing your girl crush away and pulling her back in.

You pull her in when you show her interest, reward her, give her appropriate compliments, smile at her, make her laugh, and touch her. You push her away when you remove your interest in her or challenge her, tease her, are challenging to get, and even feign dislike. 

You can't only push, and neither can you only pull. You need to balance the two behaviors, rotating between them to generate the flirtatious desire you want. And it would be best if you used all the flirtation principles to do so. 

For example, if she drops something, you can tease her about her clumsiness, playfully saying that you could never trust her with your heart. Or you could mention that her hair looks great today, implying she'll need to work hard to have it looking great tomorrow. 

You might also tell her playfully that you're lucky she isn't your type. Otherwise, you would have no option but to kiss her. 

When making these remarks, you might touch her lovingly, wink at her, or smile knowingly, so she knows you are playing. After a minute, you might also tell her you are playing, so there is no doubt.    

You should only use push/pull appropriately because it is a manipulation technique that can become abusive if taken too far. It works because two people in contact desire to be connected and validated, all basic human desires.

When using this technique, you never insult or get serious about a person's flaws or behaviors. You use it playfully, in a teasing and flirtatious manner only. 

Conclusion - Knowing You Are Successful

happy couple kissing

You'll know you are a successful flirt when your girl crush responds positively to your advances. 

While in conversation, she'll display open body language, smile, laugh, and maintain healthy eye contact. She'll also be teasing you in return, to see if you can handle the same push/pull techniques you're flirting with her. If you're lucky, you are gently touching each other and maybe even tempting a kiss. 

At this point, remember to cut it short, get the telephone number, and leave her wanting for your next encounter. Yes, say goodbye to your crush on a high note, the only way to end a successful flirting session. 

Frequently Asked Questions

These are the questions most frequently asked by our readers.

1. What are some tips for approaching a woman for the first time?

Confidence, respect, and a friendly attitude are essential. Approach her with a smile, make eye contact, and start a conversation about something you both have in common.

2. How do I know if a woman is interested in me?

Look for signals such as prolonged eye contact, smiling, and engaged body language. If she seems uninterested, it's best to back off. It's important to respect her boundaries and personal space.

3. What is the best way to start a conversation with a woman?

Ask open-ended questions about her interests, opinions, or thoughts on something relevant to the current environment. Avoid making assumptions or asking personal questions too soon.

4. How can I make a woman feel special while flirting with her?

Pay attention to her, listen to what she has to say, and genuinely compliment her. Make her feel heard, valued, and appreciated.

5. What are some common mistakes men make while flirting with women?

Being aggressive, creepy, or inappropriate comments can turn women off. Also, being overly self-absorbed, not paying attention to her reactions, and not respecting her boundaries can be flirting faux pas.

6. How can I take flirting to the next level?

As long as both parties are comfortable and willing, you can gradually escalate the level of flirtation through physical touches, such as a light touch on the arm, or by asking for her number or suggesting a date. Again, respect and communication are essential.

7. Is it okay to use pickup lines while flirting with a woman?

Pickup lines can be seen as cheesy and cliché and may not always work. It's better to be genuine and spontaneous in your conversation than rely on a rehearsed line.

8. What should I do if a woman rejects my advances?

Rejection is a normal part of dating and can be disappointing, but it's essential to handle it gracefully. Accept her decision with respect and dignity, and move on without hard feelings. Remember, not everyone will be interested in you, and that's okay.

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