For me, msn is an entirely distinct area of game.

For girls that you have on your list that you're targetting, or that you even like (pardon the one-itis), does anyone have any general tips for engaging in convo with them? How often should you talk to girls that you're interested in? Is it a bad sign if they don't message you on a regular basis? Would I come across as needy if I msg'd often (say..once a day)? What are some IOIs that are detectable over msn? How do you initiate game over msn?

Any comments would be great

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To all the women I've talked to in at parties, bars, malls, airports. I wasn't just running game on you...you were different.

I share the same questions.
I'll even add one:
What can you do to make her initiate the IM conversation first, without asking her overtly in real life, to IM you later??

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16 years old and looking for help.

Instant messenger should be used sparingly. You should let her message you every other time, or wait several days. If you build enough attraction she might even say something like "Oh so I have to message you first every time now huh?"

Engaging convo:
use an interesting question, dhv off it if you can.
DONT DONT DONT say "whats up?" because you'll get back "nm" or best case scenario "nm you" unless the girl is already attracted.

Dont talk to her too much. she should i/m you first every other time. if not wait at least 24 hours before starting convos with her. 48-36 if you've got a pair.

if they dont message you regularly you need to build more attraction.

yes, messaging every day would be needy, unless you keep the convos short, under 20 min, and leave her wanting more.

and are your IOIs sometimes you need to use one first then they start pouring out.

initiate game? look at the text message openers, same concept. "Hun is a pretty ambigious friend/potential lover term to call her. just use it like a neg and immediatly move on before she can analyze it too much and get weird about it.
Her: hey
You: what up hun?
her: nm or "not much, you?"
You: routine/interesting question/freeze out (if she says nm and doesnt say anyting else thats usually a bad sign)

and The_Shadow: if you expect her to IM you first, thats like waiting for her to call. Dont do it, you have the dick you hold the cards.

Personally I think using MSN or any other IM too often can make it look like your not a very busy person, unless you are doing it (or using the excuse) that your at work or in education (i.e. college, university, library doing course work etc). So if you do add a HB to msn and start talking with her make that first encounter as interesting and intriging to her as possible. Then leave it a day or so before logging on to the IM again. When/If she is online again she will probably initiate conversation with you and even ask where have you been for the past day or so. You just reply with anything along the lines of being busy (its good to of been busy doing something interesting i.e. you went sky diving or work trip or something but dont over exagerate things) and that you dont use IM often. She may even ask you for your phone number if she finds you that interesting to talk to and her knowing the fact that your a very busy guy who rarely uses IM makes her want to get a more viable means of contact with you (speeding this whole number exchang process up)