yes u can, but 1st u shud understand following things.

First of all check these.

1)Where does he stays?
2)Can u access his PC? (Physically or remotely)
3)He trusts u?
4)He tells u everything?
5)And what kind of relationship ur in? Just TP or serious?


the best thing wud b
BE A SOCIAL ENGINEER

or else

u can fool him easily.

1) just send him phishing page where he will enter his private data such as username/password. (I hope u know what is phishing n how 2 do that)

ELSE

2)If u physical get access to his PC, install a keylogger(Ardamax or Perfect keylogger) on his PC and configure it such that it will send each and every report(Keystrokes and screenshots of his screen) to ur mail ID.

ELSE

3)Use trojans/backdoors to get remote access to his PC.

If u ask me, ill go for 3rd method i.e, Trojans/Backdoors
i think its d best.

phishing is very weak, as nowadays few people r getting phished.

2nd method i.e, keylogger is also good but u require patience n uill have 2 check each n every e-mail.


Go 4 3rd method.

being a social engineer is not so easy and is very tedious process, as u shud have a lot of patience and uill have 2 build ur trust around him.

I hope ur familiar with all these terms (Phishing, social engineers, trojans/backdoors, keyloggers)
If not, then soory, cant explain each n everything in details.

Information about the above topics is der on our forums.
Go n read them.


I AM NOT TRYING TO HARM ANY RELATIONSHIP BETWEEN U n UR BF
I JUST REPLIED TO YOUR ANSWER.

IF ANYTHING GOES WRONG BETWEEN U N HIM, IM NOT RESPONSIBLE.

*sorry for my bad english*
as im alone handling 5 projects (VB, MIS, IS, ASP, SQL Connectivity) at a time, so i dun get much time, i wrote this in hurry.