1. Eye Contact
Eye contact is perhaps the most important thing you can do to initiate flirting. Look into the person’s eyes, but break eye contact to keep things from getting too intense. Look long enough to “get caught” looking, but do not stare, as this comes off as needy, desperate or creepy. Continually throw small glances his way until he catches you. Hold his gaze for a second, smile and then look away.
Look into his eyes when you talk, particularly at meaningful points in the conversation, for example, while you give him a compliment.
Winking or raising your eyebrows at him can be very effective – if you do it just once. Wink or raise your eyebrows while looking at someone from across a room or if you’re talking in a group and say something really meant for him. Doing it more than once comes across as cheesy or too much. Similarly, eyelash battings can come across like you’re trying too hard.
Smiling can be flirtatious in and of itself. Smile when you want to communicate to someone that you like them. Try smiling his way as you walk past or across the room from him. Don’t grin from ear-to-ear, just a simple, even subtle smile will do the trick. 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. Slow, languid smiles are often 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.
Try smiling with your eyes, not just your mouth. Make your whole face light up when you smile.
Smiling is one of the things that distinguish flirting from cruising.
3. Initiate Conversation
Whether you already know the other person or not, a conversation is a powerful way to move a flirtation forward. Striking up a conversation conveys you are bold and confident. Here are a few guidelines.
i) Talking with someone you don’t already know?
Strike up a conversation with an observation which ends with a question:
“I can’t believe how much it’s rained this week, can you?”
or “This place sure is packed, eh?”
What you say isn’t what’s important — you are simply inviting the person to talk with you.
ii) Talking with someone you do know?
Strike up a conversation based on a shared experience or interests. 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 to interact with you.
Gauge the response. If he responds pleasantly, continue the conversation. If he doesn’t respond or seems preoccupied or disinterested, he isn’t interested in flirting with you.
4. Keep it light, playful and relaxed
Don’t bring up anything too personal. Talk about the environment around you or the show you just saw. Keep personal information such as religion, money, relationships, education, and so on out of it for now. Avoid debates. Discuss topics you both don’t have a too personal stake in.
It’s easier to flirt when you’re talking about fun, light-hearted topics, such pets, silly TV shows, or your favorite spots to walk in the city. This doesn’t mean you have to dumb yourself down to flirt, but it does mean you have to relax and avoid the deep talk for a while.
Be playful, a little bit silly and relaxed.
5. Use Body Language
Non-verbal cues often communicate more directly about how you feel than what’s actually coming out of your mouth. Try the following:
Keep your stance open. Uncrossed arms and legs are signs that you are open and relaxed with the person. Crossed arms and legs convey that you are closed off them and feeling defensive.
Keep your head up, chest up, shoulders down. This communicates confidence, relaxation and alertness, which is very sexy. Head down, chest folded, shoulders hunched communicates fear.
Turn your body towards him. Stand or sit so that you’re facing the guy you’re flirting up. Angle your torso or feet in his direction.
Touching yourself in specific areas of your own body can convey flirting.: your face, neck, shoulders (e.g. fussing with your shirt), and lower legs (e.g. hugging one of your legs while sitting on grass).
Stroking your hair, rubbing the back of your neck are common flirtatious gestures. They often convey that you want him to know you’re nervous because you are interested.
Flirtatious self-touching is not overtly sexual: it does not target the chest area, crotch, thighs, ass, or involve the inside of your mouth. Using self-touch in these areas while flirting is aggressive and you run the risk of offending people. This is more appropriate for cruising and best suited for hook-up sites, bathhouses and dance clubs.
Revealing your armpits is somewhere on the border between Flirting and Cruising.
6. Touching Others
Building upon the previous flirting strategies, touch others is a way to flirt. Casually initiate physical contact by touching him on the arm or shoulder as you talk. Flirtatious touch takes places only on specific areas of his body that could be also construed as friendly touch: shoulders, upper back, outer arms, sometimes the knee. These areas convey a sense of choice. Flirtatious touch of others does not take place on more intimate areas: stomach, lower back, inner arms, neck, face, thighs, ass, inner leg, near the groin, or chest.
When using touch to flirt, do not trap, grab or grasp. Contact should be long enough to be more than accidental, but no more. Little gestures like brushing off imaginary specks of dirt off their arm, or accidentally bumping legs in a movie theatre while not moving away.
As a rule, flirtatious touch implies that rejection is okay, and welcomed without offense.
7. Compliment Early On
Compliment him at your earliest opportunity. This conveys the intention to flirt, and also gives him the opportunity to communicate with you his interest or disinterest. Not complimenting conveys you are interested in just being friends. Flirtatious compliments are more about warmth versus hot, easy-going versus aggressive, generous rather than demanding and confrontational. 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 the compliment seem intimate and sexy. Plus, it might also coax the other person to come closer to hear you.
Compliment him on his interests. It will be more meaningful.
Be careful about complementing physical features. Start with: Eyes, smile, hair, hands, laugh, voice and be cautious about more intimate things.
8. Limit length of flirtations
Keep interactions brief. Successful flirting creates a bit of mystery, and curiosity, as well as implies that you are engaged in pursuing meaningful day activities. A powerful way to generate this is to not interact with the guy you are interested in every single moment of every day. Starting off with initiating contact with him a few times a week builds interest, excitement and momentum.
Limit initial flirtatious conversations to 5-10 minutes. It’s easier to build excitement if you exit a conversation a little bit before it ends on its own.
9. Invite him to come to you
After you’ve put it out there with several instances of flirtatious interactions, it’s good to pull back a bit and see if he seeks you out for an interaction. Guys typically show their interest – or disinterest – directly. If he doesn’t seek you out for furthering flirting, he is probably not interested. This can be a good way to gauge interest, as well as build tension.
Flirting is, after all, an invitation for him to flirt back with you. Flirting offers a gentle and polite refusal when we are not interested in another’s’ advances. That is a part of one of its useful functions. Let yourself feel good about practicing and becoming better at it.
A common flirting strategy is the “double-back.” When a guy is walking towards you, or you him, make eye contact and smile. Keep his glance until he passes. Once he does, look over your shoulder and see if he is also looking back. If he does, slowly turn around, stop and maintain eyes and smiling. If he doesn’t look back the first time, do it again. If he does the same, use your flirting conversation skills to get things going. If he doesn’t, he’s probably not interested.
10. Make a date
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 him if he has plans at a later time. For instance, you might say:
“So, what are you up to on Saturday night?”
Make this invitation an open-ended question, instead of one that requires a yes or no answer — you’ll get more information that way. Don’t ask someone what he 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 or pushy.
Suggest a specific event, and ask if he 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 confident and good about your flirtation, by all means directly say to him:
“I’d really love to take you on a date. When are you free?”