| well it'd be ideal to talk on the phone or in person, so if you can manage to use IM to get her to meet in person that is best,
having said that, its really hard to convey emotion on IM, so keep that in mind. also keep in mind that tone and emphasis do not come across well on IM. i think if anything, you should keep IM for building a bit of comfort, having simple conversation, and as you said coming across as funny and confident - however, I'd say save your best game for in person, because you really need that emotion and tone in your voice, combined with kino, to help things progress. i like to keep topics on friendly topics (hence not so much flirting online) of some really amazing things going on in my life. i try to keep flirting to in person..because sometimes people can be slow to respond or might leave you halfway through conversation, which can kill your flow if you're trying to flirt it up online. when it comes to online, i stay more of a mystery to girls, it contrasts well with when they meet me in person and i give a bit more attention. then when they talk to me the next day, i'm a bit more 'preoccupied' with other things in my life. this is my personal style, other people may choose to continue hardcore gaming even online.
you can also keep details that keep her asking for more...such as instead of 'we had a wild night last night, we went to this CRAZY party at neil's house and there was so many hot girls!', i'd be like...
'we had a wild night last night!'
(let her continue the conversation with something like "oh? tell me")
then you continue on with another detail, leaving a hook at the end of sentences.
as well i also like to keep conversation short if possible, maybe tell her after a bit of discussion, randomly cut it at a highnote and say 'hey - i'm just heading out for coffee with a friend, i'll talk to you later k?' and leave. maybe come back a few hours later, check if shes on and maybe start it up again. or not...no big deal.
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CHAT