While there has always been an art to flirting, the electronic age requires a whole new set of techniques. Flirting via text message is a contemporary courtship art with its own set of rules, benefits and potential pitfalls. To flirt via text message, combine classic flirting moves with strong text communication etiquette and skills. Charm him through the art of the short message.
Less Is More
Most importantly, remember that with flirty texting, less is more. Make it your aim to give him just enough to keep thinking about you without texting so much that you seem too available or worse -- desperate or dangerously uninhibited. Especially at the early stage, make him wait a little while for each of your texts and avoid sending him more than one text without him answering you. Try to make him text more than you do, but make yours good and juicy to make up for this imbalance and keep him interested.
Taking Cues, Giving Cues
Flirtation, whether over text or otherwise, is often a matter of giving each other subtle cues that it's okay to heighten the sexy or suggestive talk, and then picking up on those cues. Each cue should only bring the level of intensity up slightly and early cues should be almost innocent but suggestive of greater closeness, like mentioning that you just got out of the shower or that you're snuggling with your pets. Feel free to use occasional emoticons like a smiley: :-) or winking face !-) to give your texts a more playful, personal touch.
Move into the territory of suggestive text slowly and only if he's picking up on your cues and moving there along with you, gradually. Try double entendres and dirty jokes, especially if you can use yourself or him as the subject of humor. Keep the comments and jokes flattering and continue to stick to a 1 to 1 ratio of his texts to your own. Show appreciation when he says flattering things to you and make it clear that you appreciate the comments because they come from him, specifically.
Humor and Connection
When in doubt, be friendly. Many of the most important aspects of flirty bonding are the same as they would be for a friendship, so include plenty of platonic references to shared opinions, interests and jokes you think the two of you may be able to enjoy together. If you find it more comfortable, feel free to focus most on your efforts to impress him and connect in this manner. Keep the more explicitly romantic side of flirting to a minimum or save it for when you're interacting in person and can better read facial expressions and tone of voice.