Not postcard related but does anyone have any advice on a good way to keep track of penpals, especially when you have more than one. Like addresses and when you have sent letters etc?
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I don’t know if it’s a great way of doing this, but I have a folder on my computer for each of my pen or postcard pals where I have a document with their address. I then take a picture of each card or letter I send them and put it into that folder, so that I know when and what I sent them 
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Spread sheet seems like a simple way of keeping track. You can have a tab for each in one document.
I have a small notebook where I track incoming and outgoing mail. I also keep addresses there. (I take photos of the pages if I’m going anywhere and will need them.)
I scan all my outgoing letters and put them in folders for each individual, along with photos of the envelopes. I used to keep incoming mail, but now I scan those too and throw the physical copies away.
keeping letters as most people put return address on envelope
Yes, I have a written list along with some notes about what I actually said in each letter or postcard so I can keep track of the progression of our conversation. And not repeat myself, lol
This is 100% why I scan them! I would probably tell the same 5 stories over and over otherwise 
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I also have a Notebook in which I keep addresses and dates of incoming and outgoing mails. Before i just had my little adressbook. That worked fine as well. Also I keep all letters in binders and have the address there as well.
A simple notebook will sort that out for you. Get something of quality such as a Dingbats A6 blank journal like this one I have here. I dare say they do lined and dotted versions too.
I wrote my penpal address in a notebook but I also have their contacts