How to Flirt

Flirting is, at its most basic, a way to get to know people you might be interested in dating. It might seem nerve-wracking to start flirting and put yourself out there, but fear not—it's normal to be nervous around someone you really like, and there are ways to seem confident and pull off a successful flirtation. Here are some pointers for flirting with someone over text, as well as in-person.

Method 1 of 2: Flirting via Text or Chat

1. Keep your approach casual. Don't let yourself get so nervous that you forget basic conversational skills. Instead, try to stay calm and open the conversation with a low-pressure way. Here are some possible openers:

• "Hey, how's it going?"
• "Did you see/hear [insert event you both know about here]?"

2. Don't talk about yourself too much. Here's a fundamental tenet of talking to people you can keep in mind: The majority of people are most comfortable talking about themselves because it's a topic they know well. Instead of taking the easy way out and discussing you endlessly, encourage the other person to talk about themselves. However, you can and should occasionally throw some personal facts in the person's direction to help them to in turn ask questions about you. The key is to leave it up to them to pursue an interest in things relevant to yourself.

• This tactic actually serves two purposes: Not only does it keep the conversation going, but it allows you to find out more about your crush.
• You don't have to possess prior information about the other person to do this step. If you don't know him or her very well yet, you can ask:
  • "How'd your day go?"
  • "So, what do you do with your free time?"
• If you do know the other person a bit, focus on a hobby or interest you're already aware of. For instance, maybe he's really into basketball, or you know she loves to read. "Did you see the game last night?" or "Have you read any good books lately?" would be great starts.
• Know when to press for more information. You can keep the discussion lively and interesting without probing too deeply on personal topics. For instance, asking your crush what exactly he or she likes about running cross-country would be a great idea; asking him or her for more details on family relationships or close friendships would be too much, too soon.

3. Compliment your crush early in the conversation. Don't chicken out and skip this step — it might seem difficult, but it's incredibly important. A compliment communicates that you're potentially interested in dating, and steers you away from the dreaded friend-zone. If you skip paying your crush a compliment and simply keep the conversation on a friendly level, it might be too late next time. Here are some basic compliments you could use:

• If you don't know your crush very well yet, but you're working on it, use a compliment oriented in this direction. Something like:
  • "You're fascinating. I LOVE talking with you."
  • "I kind of can't believe I'm getting to know someone as gorgeous and interesting as you."
• Use your crush's other interests to your advantage. If you know this person is dating (or interested in) someone else, you can use this to your advantage in a compliment.
  • Say something like, "I hope [other person] knows how lucky he/she is to be dating you."
  • Or, if that person comes up in the conversation, you could jokingly throw out something like "I'm super jealous of [name], he/she has something I REALLY want ;)". If your crush presses and asks what it is, play coy and say something like, "I can't tell you, but it's about someone beautiful/amazing/talented/[other adjective]."
• Try weaving the compliment into the conversation. For instance, if the girl you like is talking about how she had a terrible day, you could say something like "I hate seeing someone as beautiful as you feel so unhappy. What can I do to help?"
• Be careful about complimenting looks. A girl might like it if you notice her eyes, but she might label you as creepy if you say she has a nice figure too soon. Play it safe and stick to these physical features:
  • Eyes
  • Smile
  • Lips
  • Hair
  • Hands
• Be bold. If none of the suggestions above appeal to you, go for broke and pay your crush a bold compliment. Try these possibilities, using the adjective that fits your crush best or substituting your own:
  • "I hope you know you're gorgeous/beautiful/amazing/my favorite person to talk to/etc."
  • "Sorry if this is too forward, but I have to say that you're incredible/an amazing person/so beautiful/etc."
• Avoid loading compliments with feelings too early. Leaving a person slightly uncertain of the extent of your feelings for them can increase your attractiveness, giving you a bit of a mysterious edge. The point is not to make the person question whether you like them at all, but to make them wonder how much you like them. This will encourage them to interact with you more in order to find out, in essence, making them pursue you rather than the other way around. This is similar to the practice of "negging" in that the goal is too convince the other person to pursue you instead of the opposite way around, however this method does not revolve around negatively manipulating the target's self-esteem, and as such is much more ethical. To achieve this, try phrasing compliments objectively rather than subjectively. Here are examples of objective vs subjective compliments:
  • "I really like your eyes, they're so pretty.". On the surface this compliment may seem fine, and it probably would be appreciated. However a common flaw in phrasing a romantic compliment is to constantly use the words "I like/love *insert trait here*". They tell the person that they've succeeded in winning your heart. This is great if you've already built up a solid relationship, but early on it can make you seem "too easy".
  • "You have great eyes, they're very pretty". Although technically both sentences are you conveying that you like the person's eyes, this one makes it more of an observation than a personal opinion. It implies that you find the person attractive but does not confirm it outright. As such, the receiver will feel both flattered and drawn to figure out how much attractive you find them.

4. Tease gently. Because you can't use body language to communicate over text or chat, you'll have to rely on your words to keep the mood light and fun. Rely on inside jokes (based on events you were both present for), sarcasm ("Yeah, I'm SURE you look like an ogre in the morning ;)"), and exaggeration ("You're probably a million times better at this than I am") in the beginning.

• Make it clear that you're kidding. The drawback of using text to communicate is that you can't always read the emotion behind the words. If you're going to flirt with someone by teasing them, make extra sure that you're implying it's a joke. You can use winking smiley faces, all caps, or exclamation points to communicate this.
  • If you've already sent something that could be interpreted the wrong way, make your meaning crystal clear. Say something like "(joke)" or "jk" to make a quick save.

5. Always leave them wanting more. As much as you might want to text this person forever, it's best to bow out before the conversation goes stale (as all conversations are bound to do at some point). The best way to avoid an awkward pause is to leave before one happens.

• Set up your next interaction before you go. Throw out something like "Hey, so I'll see you around tomorrow?" or "Text me again sometime."
• Note that you enjoyed the conversation just before you leave. It doesn't have to be complicated — a simple "This was awesome" or "I had a good time talking to you" is enough.
• Be careful not to over-compliment them. Your compliments will have a lot less meaning if you bestow them for every single positive trait the person has. Instead reserve them for meaningful things that are important to the person, such as complimenting a skill they take pride in.

Method 2 of 2: Flirting In-Person

1. Make eye contact. Eye contact is the best and easiest thing you can do to start flirting. Consider using it in these ways:

• Get caught looking. Don't stare, but do throw small glances at someone. Keep doing it until he or she catches you. Hold the gaze for a second, smile, and look away.
• Look into his or her eyes when you talk, particularly at meaningful points in the conversation (for example, while you're paying a compliment).
• Wink. It's cheesy, but it works if used sparingly. Do it when you're looking at someone from across a room, or if you're talking in a group and say something really meant for him or her.

2. Smile. You'll probably smile automatically if you're talking to someone you like, but you can use your pearly whites to your advantage before the conversation even starts. Try these variations:

• Smile slowly. If you're looking at someone but not talking to them, try letting a slow smile spread over your face instead of breaking into an insta-grin. It's hard to say why, but slow, languid smiles are generally considered sexy.
• Smile when you make eye contact. If you're suddenly looking into someone's eyes, toss in a smile for extra appeal. (If it's a genuine smile, the other person will see it without even looking at your mouth — it will crinkle your eyes, and is known as a Duchenne smile.)

3. Start talking. Take the next opportunity to casually say hello next time you see this person. You don't have to commit to a full conversation — acknowledging him or her in passing as you walk by can be sufficient for a first contact.

• Make a habit of verbally acknowledging your crush. This can lead to conversation later.

4. Introduce yourself — or maintain the mystery (optional). If you don't already know the person you're flirting with, an introduction (or lack of one) can be a great thing to build flirting around.

• If your crush doesn't know your name and you're a naturally gregarious person, try introducing yourself at some point. It can be as simple as, "Hi, I'm [name]. And you are...?" Make sure you get the other person's name. To help yourself remember it, try repeating it after he or she says it to you. (Such as "Lily. I love that name.")
• Or, if you want to make yourself seem like a bit of a challenge, work to keep your identity a mystery for a little while. If the other person really wants to know, he or she will ask around or keep pursuing you.

5. Initiate a conversation. Whether you already know the other person or not, a conversation is the best way to move the flirtation forward. Here are a few guidelines:

• Talk to someone you don't already know. Perhaps the best way to strike up a conversation is to start with an observation which ends with a question: "Nice day, isn't it?" or "This place sure is packed, eh?" What you say isn't important — you are simply inviting the person to talk with you.
• Find common ground with someone you do know. If you've already met the other person, strike up a conversation based on a shared experience or interest. For instance, you might talk about a class you're taking together, or the train you both take to work. Again, the topic itself doesn't matter — what matters is that you're inviting him or her to interact with you.
• Gauge the response. If the person responds pleasantly, continue the conversation. If the person doesn't respond or seems preoccupied or disinterested, he or she probably isn't interested in flirting with you.
• Keep it light. Don't bring up anything too personal when you're talking. Talk about the environment around you, the show you just saw, etc. Keep personal information (such as religion, money, relationships, education, and so on) out of it, unless the person enjoys intellectual debates without becoming over-emotional. Generally, it's best to avoid debating topics personally relevant to either of you (such as either yours or their religion), and to rather discuss topics you both don't have a personal stake in.

6. Use body language to communicate your intentions. Non-verbal cues can say a lot more about how you feel than what's actually coming out of your mouth, so make sure you're communicating how you feel. Try the following:

• Keep your stance "open." Don't cross your arms or legs, as these are generally signs that you wish to isolate yourself from the other person.
• Turn your body toward the other person. Stand or sit so that you're facing the person you're flirting up. Angle your torso toward him or her, or point your feet in that direction.
• Break the "touch barrier". Casually initiate physical contact by touching him or her on the forearm as you talk, or by "accidentally" walking too close and brushing up against the other person.
  • The first few times you touch your crush, be careful not to "trap" them. Depending on the area the contact should be long enough to be more than accidental, but no more. Avoid grasping a hand or arm, and instead try gestures such as brushing an imaginary speck of dirt off of their arm, or "accidentally" touching feet or knees without pulling away. All of these touches can be rejected without humiliation or offense, so if your crush is not ready for that kind of contact, you will not be forcing them to reject you entirely.
• Play with your hair (girls). Playing with your hair is usually a sign of nervousness, which is a good thing if you like the other person — you almost want him or her to know you're nervous, because it means you're interested. To consciously communicate this, slowly twirl a strand of hair around your finger as you talk.

7. Compliment the other person early in the conversation. It might seem too forward, but letting him or her know you're interested in dating before a solid friendship begins is the easiest way to detour around the friend-zone. Get confident, anddon't let the opportunity slip by — you never know when you'll get another one. Here are some techniques to try:

• Maintain eye contact while you're complimenting. Looking away might accidentally make you seem insincere.
• Lower the tone and volume of your voice slightly. Paying a compliment in a slightly lower register than your usual speaking voice makes it seem intimate and sexy. Plus, it might also coax the other person to come closer to hear you.
• If you don't know your crush very well yet, but you're working on it, use a compliment oriented in this direction. Something like:
  • "You're fascinating. I LOVE talking with you."
  • "I kind of can't believe I'm getting to know someone as gorgeous and interesting as you."
• Use your crush's other interests to your advantage. If you know this person is dating (or interested in) someone else, you can use this to your advantage in a compliment.
  • Say something like, "I hope [other person] knows how lucky he/she is to be dating you."
  • Or, if that person comes up in the conversation, you could jokingly throw out something like "I'm super jealous of [name], he/she has something I REALLY want." If your crush presses and asks what it is, play coy and say something like, "I can't tell you, but it's about someone beautiful/amazing/talented/[other adjective]."
• Try weaving the compliment into the conversation. For instance, if the girl you like is talking about how she had a terrible day, you could say something like "I hate seeing someone as beautiful as you feel so unhappy. What can I do to help?"
• Be careful about complimenting looks. A girl might like it if you notice her eyes, but she might label you as creepy if you say she has a nice figure too soon. Play it safe and stick to these physical features:
  • Eyes
  • Smile
  • Lips
  • Hair
  • Hands
• Be bold. If none of the suggestions above appeal to you, go for broke and pay your crush a bold compliment. Try these possibilities, using the adjective that fits your crush best or substituting your own:
  • "I hope you know you're gorgeous/beautiful/amazing/my favorite person to talk to/etc."
  • "Sorry if this is too forward, but I have to say that you're incredible/an amazing person/so beautiful/etc."

8. Keep your interactions short and sweet. Remember that the key to creating demand is making supply scarce, so try to limit your interactions with the object of your flirtations. Consider these limits:

• Don't talk to him or her every single day. Make it a special event and save it for a few times a week.
• Don't let conversations drag on for more than 5 or 10 minutes. The longer they go on, the higher your odds of running into an awkward silence.
• Let the other person come to you. After you've put in the work of starting up the interaction and sparking an interest, pull back a bit and see if he or she seeks youout for an interaction. This can be a good way to gauge interest, as well as build tension.

9. Close the deal. If your flirting has been successful so far, and you want to get to know the other person better, it's time to see if you can turn it into a date. Here are a few approaches:

• Ask if the other person has plans at a later date. For instance, you might say, "So, what are you up to on Saturday night?" Try to keep this an open question, instead of one that requires a yes or no answer — you'll get more information that way.
  • Don't ask someone what he or she is doing tonight, or even tomorrow. Try to schedule the date a few days out so that you don't come off as overly desperate.
• Suggest a specific event, and ask if he or she would like to come along. This is the best approach if you're trying to arrange a group date. You could say something like, "So a bunch of us were going to see a movie on Friday, and I'd really like it if you came with us."
• Be straightforward. If you're feeling extra confident, go in for the kill without any pretense. For instance, you could say something like, "I'd really love to take you on a date. When are you free?"

10. Don't take it too seriously. Keep in mind that flirting is supposed to be fun, and try not to be crushed if your efforts aren't successful — not every interaction will be a perfect 10. Stay positive, and try again with someone else. As with anything else, flirting improves with practice.

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TIPS

• Don't complain when flirting. Remember, the world does not revolve around you. If you complain too much, others will find you depressing and avoid you. This also goes for constantly insulting yourself, which is not humble — it's another form of self-absorption.
• Don't use your phone (that means no texting) while you are flirting with someone. This shows that you are more interested in talking to somebody else who isn't there or that you are already involved in a relationship.
• If you're flirting with a girl and thinking about breaking the touch barrier, test the waters with impeccable manners. For example, offer your hand when she might need to keep her balance, such as when she's getting into or out of a car, or when she's stepping over a puddle or any other uneven surface. How does she respond when you offer your hand? Does she seem receptive? Or does she hurry to let go?
• Use flirting that is appropriate for the setting. Meeting at a library or loud dance hall, for example, might not be conducive to talking too much. In this case, smile, act interested, and wait for a spontaneous opportunity to meet at the punch bowl or in the lobby. Do not however, follow them around for a while because you're too nervous to approach the person; this will make you seem creepy. Talk to them the first chance you get.
• Don't flirt with someone you're not romantically interested in, unless you are 100% sure that they are not romantically interested in you. Otherwise, you risk accidentally leading them on, which can lead to an embarrassing moment and uncomfortable interactions afterward.
• Let go of any neediness you might have. Neediness is a precursor to obsessiveness, and obsessiveness is creepy. Needy people are imbalanced and unstable people, because their happiness hinges too greatly on someone else, rather than a stable sense of self worth. If you're projecting a vibe that you'll be devastated if a person doesn't want to be your friend or romantic partner, the lightheartedness that makes flirting fun will be extinguished.
• Flirting is not appropriate everywhere. Funerals, for example, are generally not good places to flirt. Flirting in the workplace is also generally a no-no. If you happen to flirt atwork, be on your best behavior, and don't press the issue if the other person isn't interested.
• If you don't feel comfortable asking for their number, try giving them your number. If they are truly interested in you they will give you a call. You could also pass them your email address.