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How to Flirt

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(Approaching at the Right Time)
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It is just a matter of friendly banter, some might say, but flirting can be difficult, emotional, and confusing, especially if one doesn’t know where to begin.
It is just a matter of friendly banter, some might say, but flirting can be difficult, emotional, and confusing, especially if one doesn’t know where to begin.
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===First Step in Flirting===
===First Step in Flirting===
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That being said, the sky is pretty much the limit as far as conversation goes. One important thing to remember is that as soon as the other person signals they are uncomfortable by trying to leave the conversation or are otherwise behaving in a way that might indicate they are in discomfort, it is best to end the conversation.  
That being said, the sky is pretty much the limit as far as conversation goes. One important thing to remember is that as soon as the other person signals they are uncomfortable by trying to leave the conversation or are otherwise behaving in a way that might indicate they are in discomfort, it is best to end the conversation.  
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Whether it’s a one time thing or a serious relationship you’re looking for, flirting is the first step. So take it!
Whether it’s a one time thing or a serious relationship you’re looking for, flirting is the first step. So take it!
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Revision as of 23:25, 16 August 2013

Learn to Flirt & Get Results

The history of flirting goes back as far as records can show us. Even in prehistoric societies a suitable mate would still need to be chosen and it is not difficult to imagine Grok trying to seduce his honey with acts of physical prowess and manly turn of grunt.

In fact, you could argue that not much has changed at all. Even the greatest love stories of our time, like Romeo and Juliet, began with a single conversation, a single moment of flirtation.

“Romeo: If I profane with my unworthiest hand This holy shrine, the gentle fine is this: My lips, two blushing pilgrims, ready stand To smooth that rough touch with a tender kiss.”

It Can Happen Quickly

Romeo and Juliet exchange only 14 lines before their first kiss so it goes to show that the quality of your flirting can make all the difference. Although you might want to avoid the Shakespearean wording, unless you happen to be at a Shakespeare festival.

Flirtation is the doorway to what might prove to be the greatest love story of all time. Or it could lead to a new friendship. Or even just a casual exchange that can boost your self esteem and improve your general social skills.

Who Wants to Flirt?

Maybe long term romance isn’t on your “to do” list. Maybe lusty courtships and fleeting romps are what you’re looking for at this current time. A large part of the excitement in “the chase” comes from the fun and playful banter that precedes any kind of actual dating or one night stand.

Regardless of your romantic wants, flirtation remains the spearhead that cuts through the individual bubble that separates us from the rest of the strangers in our day to day lives.

What is Flirting Really?

What is Flirting REALLY About? Flirting might be considered the most rudimentary form of courtship, the most initial form of contact between two persons who share a basic attraction toward one another.

Flirting is defined by Websters as: 2.a. To behave amorously without serious intent. But while Webster’s Dictionary can break it down into simple terminology, it is anything but simple and straightforward.

It is just a matter of friendly banter, some might say, but flirting can be difficult, emotional, and confusing, especially if one doesn’t know where to begin.

First Step in Flirting

So let’s begin at the beginning. Flirting can take place at any time and in almost any place. Many people have different definitions of what constitutes “flirting,” which can make it a confusing place to start.

Can a mere conversation count as flirting? What about a friendly touch on the shoulder or an increased level of laughter and giggles? What really constitutes a genuine flirt session?

The act of flirting is a conversation, action, or even a look, which implies there might be more than just superficial interest. Body language is the most important part of communication and the same can be said for flirting.

What Matters While Flirting?

The way you position your body, the expression on your face, and the way you move your hands, are all silent signals to the other person that flirting is your intention. And really, intention is what counts the most here.

If you intend to flirt with someone then the following conversation can be called flirting if the other person responds with at least equal participation. If they rebuff you or make an attempt to pull away from you, it is important to cease all attempts. Anything more than this can be construed as harassment.

So How Do I Know? Some people are oblivious to the attempts of others to flirt with them because they are not cued into the signals of flirtation.

Signs of Flirtation

Some general signs that someone might be trying to flirt with you:

  • Standing or leaning closer to you
  • Playing with their own hair while you are speaking to them
  • Arms are not crossed in front of them, posture is open and facing you
  • Wide smiles or what might be described as a “playful smirk”
  • Any kind of physical touching, as in picking a piece of lint off your sweater, touching your shoulder, offering a hug in greeting or in farewell
  • Laughter that seems higher than usual or in excess of what might be normally encountered in conversation

But these are just a few of the signs. In meeting a person who is a relative stranger, it is difficult to gauge what might be normal behavior for them and what might be an attempt to flirt. How to differentiate? Respond! How can you respond?

  • Joining in the laughter
  • Returning with a physical brush of your own
  • Turning the conversation toward shared interests
  • Asking questions about the person, showing interest in who they are
  • Sharing information about yourself that can lead to more than superficial conversation
  • Asking their name and where they work

These are all excellent ways to continue the potential flirt session. Your body language and how you approach and interact with the person is your first point of contact.

First impressions do make all the difference but your ability to hold a conversation and to hold the person’s interest is what will make a first impression a lasting impression. The quality of your conversation is the secondary most important part of flirting.

Saying What Matters

Some people will argue that it doesn’t matter what you say, it’s all about how you say it. While this is true in the context of body language, the quality of conversation does count for a lot when it comes to flirting with potential strangers or even well known friends.


No one likes a stick in the mud, so staying with light conversations of shared interests is the best way to continue flirtatious conversation. If it is someone that you have known for a while, you’ll be able to directly tailor your flirting with what you already know about the person.

It helps to have remembered little details about your friend. Nothing is more attractive than feeling someone is listening to you. With a stranger, it can be more difficult but it is always possible.

Focus on the Conversation

Like making a new friend, it sometimes helps just to focus on having an open conversation, like two regular human beings. Having conversations about shared interests can trigger conversations about almost anything. It also creates a great segue way into an invitation to see the person again. As an example:

You: It’s so great to meet another “Rhinestones and Kittens” fan!

Flirt: I KNOW! So many people don’t appreciate good music when they hear it!

You: Well, I’m not about to let an opportunity pass me by. Would you like to appreciate the music with me at their next show Downtown? I can get us tickets (charming smile)

Flirt: I don’t normally go out with strangers but then again, most strangers don’t have such excellent taste in music. Okay, here’s my number (scribbles it down on a napkin)

Here you have created an atmosphere of shared delight and an opportunity to see this person again. And the best part about using this approach?

If you decide during the course of the date that this person might not be an ideal candidate for romance, you have at least gained a potential friend with a shared interest. Never again will you have to endure a concert alone!

How to Generate Conversation

For those of us who lack a silver tongue or who become very nervous when they discover flirtation is occurring, there are many ways to deal with it. The first way and possibly the most effective, is to ask questions.

Most people enjoy the chance to talk about themselves and asking questions that require more than a simple “yes” or “no” answer is a great way to engage the person while avoiding putting yourself on the spot.

The important part here is to actually listen to what the person is saying, instead of just prepping yourself for what you’re going to say next. You’ll look like a fool if you’re unable to repeat what they’ve said or respond because you were too busy thinking about how nervous you are.

And relax! Easier said than done. Here are some tips on how to relax yourself when you are beginning to feel nervous:

  • Take deep breaths: in through your nose, out through your mouth
  • Count to ten in another language, it forces you to concentrate
  • Ask the person a question to let them talk for a minute

Remember: fake it until you make it. Sometimes pretending to be confident translates perfectly to another person. They can’t read your nervous mind!

Topics to Avoid

There are some topics in which to avoid during your initial, or even in follow up, conversations. Beware, talking about the following subjects can be hit or miss. On some occasions, it has a beneficial effect on your conversation.

But too easily it creates a judgment and it may not be the judgment you’re hoping for. In general, try to avoid conversations about:

  • Ex relationships and bad romantic experiences
  • Dirty, racist, or otherwise offensive jokes, until you’ve gauged their comfort level with that kind of subject matter
  • Sexual conduct or sexual expectations (unless you’re just looking for a hook up)
  • Political, religious, or highly controversial subjects (unless they are a primary criteria)
  • Negative topics in general – speaking negatively is less attractive than talking about subjects that you are positive and passionate about

That being said, the sky is pretty much the limit as far as conversation goes. One important thing to remember is that as soon as the other person signals they are uncomfortable by trying to leave the conversation or are otherwise behaving in a way that might indicate they are in discomfort, it is best to end the conversation.

If the person needs to leave, let them. Pestering them or begging them to continue in conversation is irritating at best and harassment at worst. Harassment is not to be taken lightly and whether they verbalize it or not, you have a shared responsibility to do your best not to make anyone uncomfortable.

What Happens Next?

Now What? Flirtation can go in a few different directions. In most cases, flirtation will be nothing more than a friendly, playful conversation. It can be a chance to practice if you feel you need it. However, there will come a time when you meet a person with whom flirtation is not enough.

Whether it is the beautiful woman who pours your coffee each morning or the mysterious librarian with his nose in books. Flirting can create an opportunity for you to test the waters, to see if this person will be receptive to your desires for more than just a conversation, and whether you two have anything in common.

If not, you will have spared yourself the momentary embarrassment of rejection. But nothing ventured, nothing gained. Let’s discuss one possible strategy in approaching such a person.

Approaching at the Right Time

Determine whether this is an appropriate time to approach the person. Your otherwise good chances could be ruined if you descend upon them at a moment they are frustrated, busy, or otherwise occupied. Make sure you choose a time where they will be relaxed and at ease.

Also beware if it is their place of employment. Many businesses frown upon flirtation if it detracts from the person’s performance or ability to serve their other customers. You must keep this in mind and either keep it brief, or attempt to bring the conversation to a different location and time.

When approaching the person, always remember to smile. Looking approachable is half the battle so refrain from creepy, stalker smiles, or “I’ve had too much coffee” smiles. Just a natural, genuine smile, letting the other person know you are happy to see them.

Begin a Conversation

Often this will be something from your immediate environment, such as, in a coffee shop: “Could I bother you for another delicious latte?” In such an instance they will most likely say yes and you can use this opportunity to comment on how much you like their coffee, or even, how you especially like the way they make your coffee.

If they smile or offer some kind of encouraging signal, you can follow up with a question such as: “How long have you been making delicious coffee?” Lame? Perhaps. But you will have to find your own ways of transitioning the conversation to something beyond a superficial standpoint.

Anyone can compliment someone on coffee but it is up to you to make the lasting positive impression. Remember to be aware of other customers, to wait your turn, and if it becomes busy, say farewell. Likewise if the conversation falters or begins to feel awkward, smile, thank them, and tip handsomely. T

Then at your next visit, you will at least have a foundation to begin from with the information you have received from your brief interaction.

When to Take it Further

If the conversation flows like melted butter and the person is giving you all the right signals, it might be time to take it one step further. This is where many people blow it or create an awkward situation. Lines like “Can I have your number?” or “What time do you get off work?” don’t work because they sound insincere and like a pick up line.

In some rare cases, this does work. For example, if you’re in a bar or club where people are more likely to seek out brief flings or one night stands. However, in this instance you don’t just want their number. You want to get to know them. At this point it is sometimes better to create a situation where they don’t have to reject you but spells out your casual interest.

Continuing with the coffee shop example: “Maybe when I come in next time you can tell me about the finer points of your degree in Linguistics. Until next time.” Smile, tip handsomely, and leave. Unless the person counters with a concrete offer such as “Well, I’m off in fifteen minutes.

I could tell you all about it then,” it is best to leave it to a follow up session. It also leaves the conversation on a pleasing, tantalizing note. Just make sure you come back the following day if possible. Absence does not make the heart fonder in these cases.

Making the Leap

At this point, unless you scored an immediate date or commitment from your previous conversation, you are at encounter number two. Here is where it will be entirely up to your discretion how you continue to engage the person. There will come a point where you’ll either have to take the leap and ask them if they want to see you outside of the usual setting or chicken out all together.

Being willing to laugh and being prepared for a response such as “Sorry, I have a boy/girlfriend,” is important. If this happens, don’t look crushed, smile and if able, laugh it off. You never know when the moment might come that the girl/boyfriend suddenly disappears.

Never destroy an opportunity or close that door. You may only gain a friend but the potential for romance can make itself apparent in the future. Remember, reading body language is very important in your flirting success and nothing ventured, nothing gained. So get out there and don’t forget to smile!

Final Tips on Do's and Don'ts

The ‘Do Not’ List

Do not flirt with someone whom there will be significant social consequences, such as your best friend’s mother or girlfriend. Though it may seem innocent enough at the time, flirting can inevitably lead to something unintended and allowing yourself to get swept up in the moment may lead to very significant consequences (i.e., a punch in the mouth.)

Do not flirt with someone you have absolutely no interest in. Leading people on can only lead to a lot of drama or at the very least, immense awkwardness should the person try and follow up on your flirtatious interactions. Rejecting someone can sometimes be as bad as being the one rejected.

Do not flirt in situations that are inappropriate: at funerals, in the middle of a movie theater, during someone’s poetry reading, or any situation that implies silence or solemn reflection. Not only will other people be irritated with your conduct you run the risk of turning your person of interest off completely.

Keep it Clean

Do not be lewd or sexually inappropriate with someone you do not know well. Even if they are a friend you have known for some time, being sexually lewd can be a big turn off for some people. Coming on too strongly can also be construed as sexual harassment. Sexual harassment, as well as harassment in general, is an issue that is not taken lightly in today’s society and rightfully so.

Don't Overdo It

Do not complain, whine, or generally commiserate during a flirtatious conversation. Remember, positive is always more attractive than negative. If a negative subject comes up, cut it off at the pass with a humorous comment like “but enough about Negative Nancy… you said you love doing Hot Yoga?”

Do not try too hard. Nothing is less endearing than someone who continues to try after you’ve made it abundantly clear you’re not interested. If you’re that someone, give it up. Continuing to be friendly and genuine are much more pleasing than the stench of desperation.

Do not show off. Arrogance is an extremely unattractive quality so you must toe the line of acknowledging your positive attributes while avoiding the urge to stand upon mountaintops proclaiming it to the world. Your person of interest does not want to hear about how awesome you think you are.

Watch the Workspace

Being in love with yourself leaves no room for anyone else. Do not flirt with people in your own workplace. This can be perceived as very unprofessional and there can be legal repercussions if the person feels you are harassing them. It can also cause complications if the flirting leads to a fling or relationship.

What happens if that ends badly? Rumors can also be started this way and can create a very uncomfortable work environment. Worse case scenario? You could be fired.

The ‘Do’ List

Do listen to what the other person has to say. Staring at their mouth, their breasts, or how good their butt looks in those jeans is a sure way to get rejected or otherwise ridiculed. Retain the ability to respond to what they are saying and continuing the conversation. Save the drooling for your own private quarters.

Be a Complimenter

Do compliment the person sincerely. Most people can see through a fake compliment and it flags suspicion more than a lack of compliments would. That being said, make it a point to notice special or pleasing things about the other person.

This goes both ways. If your person of interest compliments you, DO accept it with a simple “thank you” or other validating response. Denying it or drowning it in explanation is not ideal. In general, do find positive things to say about yourself and the world at large.

Do find common ground with the other person. Diversity is the spice of life and while you and the person may have many differing interests, finding some common ground can bring you closer together and lay a foundation for a friendship should romance fail to develop between you.

Using Body Language

Do use your body language to convey interest. While forcing a laugh at their lame jokes might come across as pretty fake, a empathic chuckle or giggle will at least let them know they aren’t striking out completely (unless they are.) Refrain from touching the person until you have had a lengthy conversation or multiple conversations.

Prematurely stepping into someone’s personal bubble can immediately brand you as “creepy.” This is one you’ll have to play by ear and sight. Different people have different levels of comfort with physical touch.

Laugh and Smile

Do have a good sense of humor about yourself. Taking yourself or anything too seriously during a flirtatious encounter can be like a lead weight aboard a row boat.

You’ll start taking on water and the conversation could be well sunk before you reach the shore. Be willing to laugh at yourself but remember, laughing at the other person when that laughter is not being shared is an equal ship sinker.

Share and Be Yourself

Do share your passions and interests. While no one likes someone who is self absorbed, if you completely avoid talking about yourself, it is another suspicious flag.

Do you keep dead bodies in your basement apartment? If not, you should make that clear by sharing all those normal and relatable interests. Try to keep more embarrassing details to yourself. Those details are only charming after the third date.

Get Out There! So the time has come to put words into action and to begin your journey in flirting. Having an understanding of body language, the importance of conversation, and the appropriate ways to flirt, will also help you in your romantic success.

Whether it’s a one time thing or a serious relationship you’re looking for, flirting is the first step. So take it!

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