Warnings

Do not flirt with someone who you are sure that you're not romantically interested in, period. Otherwise, you risk accidentally leading them on, which can lead to an embarrassing moment and uncomfortable interactions afterwards. But still remember that you are not getting married, yet. Flirting is like compliments, in that it should have a kind of sincerity attached to it. Flirt with people who seem different than you or who you do not know much about, and they could surprise you.

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, appear to be a stalker or you will scare them away.

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 at work, be on your best behavior, and don't press the issue if the other person isn't interested.

Though humor is often a good way to flirt with people, try not to make any jokes that might make your flirting recipient uncomfortable. Though dirty jokes often come to mind when flirting with someone, they often have little or no place in a conversation and can result in the person being turned off or an awkward silence, killing the mood and making you feel embarrassed. Think before you speak, and remember, you don't have to be funny all the time.