Flirting via text messaging can be very fun and exciting. It's like of the grown-up version of passing notes to each other in class. Take into account, however, that since texting is non-verbal, the message can be easily misinterpreted. Remember not to take it too seriously and just have fun playing around.
Text When Sober
Equivalent to the old "drunk-and-dial" plaguing college freshmen for centuries, it's one of those things that always seems like a great idea at the time, until you cringe the next day reading what you wrote. Alcohol impairs judgment, making it especially tempting to connect with the hottest person in your address book. If you do get a little tipsy, have a trusted friend hold onto your phone for the night. You'll never regret NOT texting someone when intoxicated, after all.
Text When Happy
Make sure you are in a good mood before texting, because your mood will come through. If you are down or unhappy, it will show. It may make you look needy, vulnerable or just be a general downer. People gravitate towards sunny people, so if you're feeling sad and needing validation, text your best friend or call your mother.
Text for Information
Have a specific goal when texting. Don't just text "Hi," as this can fall flat and not easy to respond to. If you want to know if they're going to the same party or event, text and ask for directions. If you can't remember the name of a band or favorite restaurant once mentioned, text and ask for clarification. Stacked openers require an answer other than yes or no and can lead to more conversational topics. It's also a relatively safe way to test the waters without coming on too strong.
Text for Fun
Unless you're already in a serious relationship, don't be sexual in your text messaging. Only flirt with innuendo when it feels appropriate, and both parties are participating. Using puns and subtext is often funnier and possibly sexier when sexuality is hinted at, otherwise it may just come off as crude and unattractive.
Text for Brevity
Keep it simple. Text messaging is for brief, concise communication. Lots of information requires an email or phone call, so keep your text messaging short and sweet. It also adds a bit of mystery and intrigue, like you're a person who has places to go and people to see. Long text messaging can be exhausting, and may seem desperate.