Well, first of all, both of you must have "chat" in LW enabled. (LW>Tools>Options>Chat)
Then both of you need to have the firewalls properly configured.
And last but not least, the direct connect function of LW isn't quite a exact science, means sometimes it works fine and other days it won't......
As for file sizes, I'm not sure whether the limit of LW is 1GB or 2GB. To be on the save side, make a split rar file to share it.
