Im running spigot 1.13 and luckperms, and ive got a bug with permissions where using the permissions nodes zh.friend zh.friend.add zh.friend.list & zh.friend.remove dont actually do anything and users are greated with "you dont have "zh.friend"

Using zh.friend.* works perfectly fine and with friend.* all friends commands are available. but the individual friend command permissions nodes dont work

That's weird, I'll try to find out what's not working.
Could you check with LuckPerms commands if someone has the zh.friend perm when you only give him this perm and not zh.friend.* ?
Also, is there something particular that you're trying to achieve by not using zh.friend.* or is it just for the sake of testing ?

I just tried giving myself only the zh.friend and zh.friend.list permissions and it works fine.
As you can seed on this screenshot, the commands /zh friend add and /zh friend remove don't appear because I don't have the required permission : https://gyazo.com/2464632d684a4d216da2e8bd7b2309a3
I'm using ZHorse 1.8.1 snapshot 2 (pretty much the same as 1.8.0 release), PaperMC 513 and PermissionsBukkit 2.5.

Make sure that your LuckPerms' config respects the file format, don't mix blanks and tabs, etc.
I'm closing the issue as I couldn't reproduce the problem but feel free to give me some updates below ;)