Flirting Dos
Start the conversation casually. As in the real world, the first step to flirting is to get over your cold feet and jump right in! Text the other person a brief message asking them about their day, asking them a specific question about work or school, or simply saying "Hi!". The hardest part of flirting is to break through your initial reluctance, so if you're having a hard time taking the plunge, just remind yourself that no matter how badly it goes, it'll be less stressful than an equivalent real-world encounter. There's no reason to be nervous when it comes to IM flirting — if the person you want to talk to doesn't want to talk to you, s/he always has the option of simply not responding to your message, as, from your point of view, this is indistinguishable from him or her simply being away from the computer. This being said, if you barely know someone, it can be a good idea to have an excuse for starting a conversation to avoid awkwardness. Asking for help with a work or school-related problem is almost always a good bet, as is asking a question about something striking about the person. For instance, if the person has a band-related username, you might say: "Hey, cool name. Did you see those guys when they last came to town?"
Start small talk. After your initial greeting and exchange of pleasantries, you'll probably want to ask how the person's doing (just like you might in the real world). Ask him or her about work or school, his/her interests, or any recent trips, for instance. Rather than asking a question, you can also simply offer your comments on these things. When s/he responds, add your own comments or ask follow-up questions and proceed from there! Don't pry into his or her personal life — keep things light, fun, and focused on worry-free subjects. Don't dwell too long on small talk. A minute or two is great for breaking the ice, but much more can get boring fast. For example, after we've opened up by asking about this person's interest in the band in his/her username, it's logical and reasonable to ask about this person's musical likes and dislikes. You can even offer your own opinions and suggestions. For instance, you might say something like: "If you like those guys, you might want to check out this band called Manic Albatross - they're like the Beatles, only darker. What sorts of other bands do you like?"
Joke. Everyone likes a good sense of humour. In the immortal words of Marilyn Monroe, "If you can make a woman laugh, you can make her do anything" (don't worry, ladies — the same is true for men!) Try to be playful and even slightly sarcastic as you respond to the statements of the person you're talking to. For instance, if you're asked what you're up to, rather than saying, "looking for people to hit on on Facebook", you might find that it's a better idea to give a sarcastic answer like "writing the great American novel" or "drowning my sorrows". These responses have the added benefit of being natural launching points for conversations about your hobbies, like the writing you're doing on the side and the great bourbon you tasted the other day. In our example conversation, you might work a joke or two into your music-related small talk. For instance, you might say something like, "I don't know why every song on the radio nowadays has a Texas Flynn feature. Does he even have time to record between rehab stints?"
Tease playfully. When you've established a good rapport with the person you're talking to, it's a good idea to up the ante by getting in a good tease or two. As you do so, maintain a playful air to keep the atmosphere light. As a good general rule, the better you know this person, the "sharper" your teasing can be. Be reasonable about your teasing. Obviously, you'll want to avoid sore subjects that have to do with this person's personal life, career, aspirations, and so on. The line between being a flirt and being a jerk can be somewhat thin at times, so, when in doubt, play it safe. It's easy to think up a different dig later, but it's not so easy to talk your way out of the situation after hurting someone's feelings. In our example, you might gently rib your conversation partner about a certain band s/he likes with a line like, "Oh, come on, them? Hahaha." However, if you say something like, "Those guys are nothing but posers and their fans are the worst", you'll sound a little more threatening.
Use cheeky emoticons. One of the handy things about flirting via IM services with emoticons as opposed to via purely text-based channels like email is that it's possible to make the intended emotion behind your words explicitly clear. If you're flirting, you'll want to rely fairly heavily on the winking (;)) and "tongue stuck out" (:p) emoticons that nearly all IM services have built in. Accompany your flirtatious, teasing remarks with these types of emoticons to make your intent obvious, yet palatable. A word of caution - don't overuse emoticons. Sprinkle them sparingly throughout your conversation to make your flirtatious jabs a little sweeter and to make the intent behind ambiguous sentences a little clearer. If you use emoticons constantly, you'll end up seeming juvenile or annoying.
If you're getting a good response, heat things up! If your conversation partner seems to be reacting with good humor to your jokes and teasing, you may want to make the transition into more intimate territory. Do this gently — don't go from lighthearted teasing into full-on come-on mode. Instead, make subtle innuendos. Imply things, don't outright state them. This is called "being smooth" and it's a valuable skill sought by many both online and in the real world. Try to stay tongue-in-cheek with your remarks. There's a certain degree of silliness to any sort of flirting or come-on. Acknowledging this silliness does a lot to make you seem more down-to-earth and less creepy. For instance, in our band conversation example, if your conversation partner says that s/he finds a certain song sexy, play along and turn up the heat. Fire back with a faux-scandalized "Behave!" or show you're game with a wry "Oh reeeally? ;)".
If you're getting a bad response, back off. Flirting with people anywhere means dealing with the possibility of rejection. Online, where communication is cheap and impersonal, this possibility is a very real one indeed. If the person you're flirting with doesn't seem to be reciprocating, cut your losses and exit the conversation gracefully. For instance, you might try saying that you have something you need to do (homework or job-related activities work well as excuses) or that you need to go to sleep. The exact excuse you use to exit the conversation isn't important — what is important is that you respect the wishes of the person you're flirting with and avoid dragging out a needlessly embarrassing exchange. For instance, in our band conversation example, if you mention a certain song and your partner says that it's his or her S.O.'s favorite song, you'll want to eventually make a polite exit. This can be as simple as typing, "Hey, I gotta run. Talk to you later!"
Be the person to end the conversation. A good rule for flirting online and in real life is to end the encounter by leaving the other person wanting more. In the world of IM flirting, this means that you should shoot a quick goodbye message before the conversation starts to grow stale. This way, the person you've been IMing with will have only fun, positive memories of the encounter — not awkward memories of struggling to find something to say as the conversation goes on and on. If your conversation partner has responded well to your flirting so far, make your sign-off a saucy one to ensure s/he doesn't forget you. Emoticons can help here. For instance, while the message "Goodnight." is somewhat plain and uninspiring, "Goodnight. ;)" can carry the subtle connotation that you'll be thinking about them (and possibly vice versa).
Flirting Don'ts
Don't be too self-deprecating. Simply put, confidence is sexy. This is more true for real-life situations than it is online, but this mantra has some truth in the world of IM flirting as well. For instance, you'll want to avoid making lots of jokes at your own expense. Just one is plenty — it shouldn't be a recurring theme throughout your conversation. Doing this too often can quickly turn an otherwise flirtatious conversation into one in which you appear needy and self-loathing. On the other hand, this isn't to say that you should necessarily make jokes at other people's expense, as this can make you seem mean and petty. Any sort of pointed or caustic remarks about yourself or someone else don't have a place in flirtatious conversations.
Don't be too sappy. People like flirting to be fun. For most people, receiving compliments is only fun up to a point — getting more than one or two can make someone feel embarrassed and self-conscious. It can also make him or her question your motives, leading the person to believe that you may be trying to get something out of him or her. Besides, the wooing power of flowery, gushing compliments is diminished (to say the least) when the compliments are displayed in a tiny box at the bottom of the screen alongside cartoon smiley faces. Instead of relying too heavily on compliments, instead, focus on having an engaging, genuine conversation. Follow the mantra "show, don't tell." In other words, show that you're attracted to this person by giving him or her a great conversation, not by stating it outright.
Don't be too clingy. Flirting with someone for the first time via IM is ample evidence that your relationship is a very, very casual one. Because of this, you'll absolutely want to keep your conversation casual. Don't bring up love, long-term commitment, or anything similar when you flirt — these are giant red flags to the person you're talking to and, in most cases, will completely sabotage your chances of eventually winning a date.
Don't be vulgar. Different people have different attitudes towards when it's appropriate to use dirty language, potty humor, sexual references, and so on. Respect this difference. Online, where bad language, violence, rude humor, and sex are all just a few clicks away, it's easy to forget that many people don't like being confronted with these types of shocking content. So, keep the conversation relatively PG until you know this person a little better. At the very least, try to be conscientious of how you may appear to the other person if s/he isn't used to these types of things. A good rule of thumb is not to be vulgar until your conversation partner is. In other words, if you're flirting with someone, don't curse, make dirty jokes, or make lewd comments until s/he does first.
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