For some lucky people, flirting is a skill that seems to come as naturally as breathing. For most, however, the art of engaging with one's preferred sex is something more of a challenge. To improve your luck in flirtation, whether you're seeking the company of men or women, follow a few essential tips based on fundamental concepts of social and casual romantic interaction.
Unless you already have an established relationship (acquaintance, casual or otherwise) with the person you want to flirt with, the first step in flirting for both men and women is to come up with a way to break the ice and start a conversation. In social settings such as bars or clubs, this is often made difficult by the fact that people are on their guard against unwanted advances. Give your target person a reason to want to talk to you by having something interesting to say to strike up a conversation through shared interests or experiences. Watch to find something you might have in common by looking at visible details, such as what she's wearing (e.g. a T-shirt for a favorite band), drinking, eating or reading. Comment on one of these, or ask a question related to them.
Once you've successfully broken the ice and found something to talk about, work the conversation in the direction of other areas and interests that the two of you may share. Discovering shared interests in activities and popular culture (the more esoteric, the better) is an excellent way to establish a connection.
Humor is an effective means of flirting in three different contexts; making the other person laugh, laughing at his jokes, and laughing at things together. Even if you don't consider yourself to be terribly witty, look for chances to laugh in the presence of your target. In addition to sharing a joyful experience, the act of laughter itself can make you appear pleasant and easy to be around.
Ask your flirting target questions about herself to show that you're a good listener while encouraging her to open up about herself so that the two of you can connect. Avoid personal questions or questions that would reveal sensitive information (such as names, addresses or places of work), but do ask safe, meaningful questions about interests, occupations and general life outlook/philosophy.