Are you and your buddy connected to the AIM network (via Pidgin or otherwise)? As far as I know, the
Direct IM feature only works when both parties are connected to the AIM network. Also over the weekend Pidgin has been updated (there is still no send button) to
Pidgin 2.1.0.
Sean talks on
Pidgin Planet about the way send works and its evolution thorough Gaim (Pidgin) history:
Enter vs. Control-Enter. In one of the screenshots you can see what looks like a Send button (i can't be sure since i know no Korean) in previous versions. Maybe they'll bring it back sometime.
Sean also mentions how you have to know what protocol your buddy is using before you send a file.
Quote:
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Of course, there are some times where it's important to know what protocol you are using, due to the differing capabilities of the protocols supported by Pidgin. We've kept the protocol icons in Pidgin, but downgraded them to secondary elements. When you know you need, for example, an AIM account to send a file to, you'll always want to find the person first, and then check the protocol.
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(the bold is mine) It is very annoying that not all file sharing capabilities are/work the same on all Pidgin supported IM networks. I do not think that this is a problem can be fixed. Different networks support different methods of transfer and not all methods are supported in Pidgin. All we lusers (endusers) can do is wait for the (unpaid or underpaid) Pidgin developers to write the code (or write it on our own).