The best times I've had with friends have always been doing inane things that don't require any planning whatsoever. Driving around Auckland with Mia, Monty Python shennanigans with Nicky, napping on Binda's bed after work at the timber yard, spontaneous street-karaoke with Dan/Danielle/Elly/Rory and sitting at the ruins on Arthur's Seat with Tara, not to mention gaming with pretty much anyone who has ever come over (special mention to Gauntlet: Dark Legacy). These times may be incredibly simple and in some cases not even full of laughter but simply just relaxing... but even so, these times are the ones that I remember far more than any heavily organised events. Just enjoy time with each other.
If you can't find the conversation, have a drink or two or do something stupid to break the ice, but once that ice is broken it should be just like chatting in #eoff or posting on the forums - come up with a conversation, let it roll, enjoy. And in some cases, with the right people and in the right moments, no conversation is needed at all. Although those times are admittedly rare.