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?”
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?”
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?”
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.
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.
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.
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.
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? ;)”.
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!”
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).
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.
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.
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.
