First of all the thread was placed in the wrong part of the forum. The tutorials board is only there for posting tutorials and howtos, not asking questions =)
Also I can start the answering of your question with giving you the rules, if you haven't already read them, they are
HERE (rules are updated, but the update hasn't been published yet). Now, this is a whitehat forum so we don't support unethical behavior, thus we can't help you with your problem.
But if you formulate your problem in a more "I would like to learn" way, then we might point you in the right direction ^^
And seeing that it's late where I am and that I am generally bored, I will pretend that you asked the question in the above way. So...
Well, first of all if your target has a Anti Virus that is fairly updated, any attempt to send him trojans that you downloaded from the web, will fail to 98%. As in he will detect your attempts and block you from msn, which means "mission failed". Also, you can rename the trojan file to an extension that does not execute the code. jpg and txt files are not executed like that. jpg is opened by an image handler and will try to read the file in another way, and txt files will only be opened in notepad and he will simply, either see the source code, or just a bunch of scrambled machine code.
So your first goal would be to social engineer him with your "cute girl" plan. And since that can take some time, I suggest you drop the trojan plan for a while ^^ and start working on gaining his trust with your female side =P
Anyway.... try to post in the right forum in the future, and mind your words when asking questions here if you want to do something either illegal or unethical =)
