Online relationships are really an extension of daily life. If you find it easy to flirt with the girl at the front desk, or the delivery guy, then you should easily be able to flirt online. However, if your like many who struggle to flirt in your daily life, there is hope, you can get good at flirting online, and who knows, it may just spill over into your offline life.
Being a flirt is about having fun, having a ton of confidence, and being bigger than life. It's really easier to flirt online than it is to flirt in person because your chat partner can not see your facial expressions, hear a quiver in your voice, or pick any weird vibes. Just as some people have "Phone Cajones" (this is where they have extreme confidence on the phone but not always in person), so you too can develop "Online Flirting Cajones" where you learn to be forceful and confident while at the same time being flirtatious and entertaining.
Now a word of caution … you want to flirt, but do not go over the top, there is a fine line between being funny and confident and being abrasive, arrogant, or over-the-top. When your flirting, you will also want to be careful about choosing taboo topics before you feel out the other person. Flirting is about starting slow and building up steam. Keep your conversation open and playful and do not be afraid to throw in some sexual innuendo if the conversation heads that direction. Your goal is to make the other person excited to talk to you again.
You will also want to have a great attitude and not be critical of others or complain. Believe me, nothing kills flirting faster than talking about your gall bladder surgery or about your "Ex". Pay attention to what the other person is saying, and key off of their queues. The more you can get the other person to open up and talk about themselves, the more you can steer the conversation towards what you most want to talk about. Just remember to complement your chat partner often and remember the saying "flattery will get you everywhere".
When you've had a great chat, do not forget to send a thank you email to tell them how witty they were, and how much fun you had. Try to bring up one of the topics that made you both laugh. This is also a great time to setup your next online date. Remember above all else that flirting is about getting to know the other person, opening the lines of communication, and having fun!