If you are trying to establish a connection with your buddy and you keep getting timeout errors, you may need to tell AIM to use your other IP address. This can be changed if you are having problems with "IM Images, IM Talk, IM File Sharing, IM Transfer, or Games".  Follow these steps to set up AIM correctly:

First bring up your AIM Preferences window by clicking the preferences icon in the Buddy List toolbar

or by right clicking your system tray AIM icon.

On the left hand side select the category you want to change the setting for.  Now find the "Use alternate Internet Address" checkbox on the right side and make sure that value is checked.

Close the preferences window and attempt to make a direct connection with your buddy. To do this, start a conversation with a buddy and click the "Connect to Send IM Image" icon in the IM window toolbar.

You should now be able to connect without timing out. If it still wont connect ensure the other buddy is able to make connections with others.