1. Lower your expectations. Flirting is fun, but only if you don't take it too seriously. Most of the time, you'll just flirt with someone for a short time and then maybe never talk to them again. If you always go in to flirting expecting to date or even marry the person you're flirting with, you're going to be very disappointed--and you'll probably seem a little desperate. Remember, you're just flirting.
Look approachable. Relax and smile. Use your body language to give signals that you are the fun person that you are, and to show that you're comfortable and confident. There's nothing to be nervous about.
3. Read body language. Does the person look approachable? Do they appear interested in you? From the moment you see someone with whom you might want to flirt, you should read his or her body language. Once you're actually flirting with the person, body language is often the only way to tell if the person is actually interested in you . We all have a natural ability to read body language, but it's easy to misread signals, so be careful and take it slow. If you see one signal that indicates the person is interested in you, watch for other signals that might confirm that.
4. Make eye contact, but not for more than a moment or two. Do not stare. Just shoot the person a quick gaze, smile with your eyes, and then slowly look away. If you look back and notice the person looking back to meet your eyes, they're likely interested in flirting a bit.
5. Initiate a conversation with the person you're interested in. If you don't already know them simply make small talk. Perhaps the best way to strike up a conversation is to start with a simple observation which ends with a question: "Nice day, isn't it?" or "This place sure is packed, eh?" are just a couple examples. What you say isn't important. You don't really need an answer to the question; you are simply inviting the person to talk with you. 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. At the beginning of the conversation, you don't want to talk about anything personal. Talk about the environment around you, the show you just saw, etc., but don't talk much about yourself and don't ask the other person personal questions.
Gradually share information about yourself in a reciprocal manner. If this small talk goes well, proceed to share a little information about yourself--just something small like what you do for a living or how you liked the show you just saw, for example. At some point, of course, you'll want to introduce yourself and, hopefully, get the other person's name. The key to sharing information is that you both gradually open up. Take turns talking, and each time the other person gives you some information about himself or herself, give similar information about yourself, and maybe give slightly more personal information than that person gave. For example, if you're talking to a girl who says she's taking summer classes, you might disclose that you are also taking summer classes, and then proceed to tell her which class you are most excited about. This invites her to disclose more information about herself. In this manner, the intimacy of the conversation increases over time. You don't want to share too much about yourself too quickly, and you shouldn't try to get the other person to do so either.
7. Give the person your complete attention. Laugh at their jokes, listen to their stories, and don't get distracted by what's going on around you. It's more important to seem interested than to seem interesting, and you don't want to hog the conversation. Being a good listener is far more important to successful flirting than being witty.
8. Use body language to hint at your romantic intentions. If things are going really well, you might want to try to break the touch barrier. Touch his or her arm briefly and gently as you talk. Or be more assertive and hold the person's hand when you cross the street, or if walking to a seat or a table, lead them by gently holding their arm. Touching in this manner helps break a "personal space" barrier. Pay attention to red flags, because some people have "personal space" issues and you don't want to make them uncomfortable. In general, women can get away with touching much earlier in a conversation than men can. Many women feel a little threatened when a man they just met enters their personal space, while most men are more open to being touched. In any case, proceed with caution, and back off if you get negative or mixed signals from the person.
Close the deal. Most flirting is just harmless fun, and nothing will ever come of it. Every now and then, though, you'll meet someone who you'd like to see again and who you think would also like to see you again. Flirting is, after all, a type of courting ritual, a way to meet