Honestly signal, I however don’t usually share anon outside of torrents

Ah yes the age old problem

If you're looking for a privacy respecting paid service that's not just a file locker for pirates I have two recommendations: At a previous workplace, we used LiquidFiles. More catered for commercial uses.

Personally I've been using Bitwarden Send. Requires a paid account ($10/year) and limited to 500MB files.

some PDF with a friend

i would probably just email it

share a PDF or a file with an anonymous lemmy user

onionShare?

protonDrive :/

For sharing with your friends you might look into Magic Wormhole. In my case I just put the file on a personal web site, usually.

Not anonymous or free but bitwarden send is nice. Thundermail from Mozilla will have this feature too.

Depends on the size. If it's small enough I send via Signal. Larger files end up on my Nextcloud instance.

I usually use croc, though it requires the receiving party to be around to receive it immediately.

Honestly, it depends. On the size of the file(s), type of files, etc. But usually either Signal or wormhole. If they're standing next to me I've used Android Quick Share.

You can use https://www.swisstransfer.com/ from infomaniak, it's privacy respecting, or https://lufi.ethibox.fr/

https://wormhole.app/

E2EE and simple

Signal or Proton Drive

SimpleX Chat can work with your friends. Don't know for anonymous sharing, Internet Archive?