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| How to Flirt Through Instant Messaging |
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| So you want to flirt with a guy or gal on MSN, AIM, Facebook Chat, or any other instant messaging service and you don't want to look like a creep? |
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| Congratulations — by seeking help, you've already demonstrated more self-awareness than the vast majority of online flirts. |
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| See Step 1 below to start flirting smartly and respectfully. |
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| Part 1 of 2: Flirting Dos |
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| Start the conversation casually. |
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| As in the real world, the first step to flirting is to get over your cold feet and jump right in! |
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| 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!'. |
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| 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. |
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| There's no reason to be nervous when it comes to IM flirting — |
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| 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. |
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| 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. |
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| 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. |
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| 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?' |
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| Start small talk. |
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| 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). |
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| Ask him or her about work or school, his / her interests, or any recent trips, for instance. |
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| Rather than asking a question, you can also simply offer your comments on these things. |
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| When s/he responds, add your own comments or ask follow-up questions and proceed from there! |
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| Don't pry into his or her personal life — keep things light, fun, and focused on worry-free subjects. |
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| Don't dwell too long on small talk. |
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| A minute or two is great for breaking the ice, but much more can get boring fast. |
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| 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. |
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| You can even offer your own opinions and suggestions. |
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| 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?' |
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| Joke. |
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| Everyone likes a good sense of humor. |
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| 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!) |
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| Try to be playful and even slightly sarcastic as you respond to the statements of the person you're talking to. |
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| 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'. |
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| 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. |
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| In our example conversation, you might work a joke or two into your music-related small talk. |
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| 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?' |
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| Part 2 of 2: Flirting Don'ts |
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| Don't be too self-deprecating. |
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| Simply put, confidence is sexy. |
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| 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. |
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| For instance, you'll want to avoid making lots of jokes at your own expense. |
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| Just one is plenty — it shouldn't be a recurring theme throughout your conversation. |
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| Doing this too often can quickly turn an otherwise flirtatious conversation into one in which you appear needy and self-loathing. |
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| 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. |
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| Any sort of pointed or caustic remarks about yourself or someone else don't have a place in flirtatious conversations. |
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| Don't be too sappy. |
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| People like flirting to be fun. |
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| 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. |
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| 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. |
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| 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. |
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| Instead of relying too heavily on compliments, instead, focus on having an engaging, genuine conversation. |
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| Follow the mantra 'show, don't tell.' |
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| In other words, show that you're attracted to this person by giving him or her a great conversation, not by stating it outright. |