I regularly spot Filofaxes in the Wild so I have just started a ‘Filofaxes Spotted in the Wild’ category.
Today’s spotting was in my classroom. This student had a pocket Tropic until it broke so now she has a pocket Malden in purple. She is going to follow my lead and use it as a wallet. She saw my Ostrich last week and liked how I used it as both a wallet and a planner. 
If you spot a Filofax in the wild I would like to encourage you to stop and ask the person about it. Believe me, in today’s digital world, anyone using a paper planner is doing so because they have made a conscious decision to go against the prevailing method of scheduling. Also with Filofaxes becoming harder and harder to find in brick and mortar shops, they have probably made a conscious decision to use Filofax. And they will more than likely be willing to chat about it. That is what I have found anyway – and I stop people everywhere!
I am in the UK, and find it’s a great ice breaker. You meet lots of fun people of all ages. I have noticed that lately many youngsters are carrying Filofaxes again.
You are right about striking up a conversation – I have been approached several times when writing in my Filofax and have had a nice chat with people. I am now on the lookout now for others who are using them 🙂