Sigh. Okay 
help please!
I’m stuck on the drinking game with the Rum dude. I can empty the mug and I can use the coloured drinks from the Bloody Lip in it, but none of these things help.
Question 1: Is emptying the mug the first step?
Question 2: Do I need to acquire (or create) some other kind of liquid to put in the mug?
Please answer yes/no (or ‘rephrase/be more specific’ etc). No extra info please! 
1 Yes, into the plant!
2 Yes!
Does that spoiler say ‘into the plant’? I didn’t want to click it just in case!
Edit: ooh yeah it looks the same shape of blur 
I haven’t been stuck on this bit the whole time by the way - I got my other map piece back 
Right. So I think I know I need to get some other liquid from the barman at the Bloody Lip, aye? Other than red, yellow or blue?
Aye. Just talk to the guy a bit more.
Hm. I keep trying that but I can only seem to order the three drinks or say I’m not thirsty.
Didn´t he offer you something before you could proof that you were old enough to drink?
Possibly, I don’t remember 
do I need to somehow pretend I’m underage again?
No, I really have to scan an imaginary puzzle tree chart now, because I´m not sure what you have and haven´t done yet!
perhaps you need to blur your questions there too…
I can’t offer too much help. I know this puzzle has me stumped every time I replay MI2 too.
Haha
Okay so here’s what I’ve done with the bartender so far (snort):
Used my library card to show I’m 21
Order three drinks (red, blue, yellow)
Mix blue and green to get the spit drink
Give my empty glass back in exchange for more of those drinks
not sure…
but then again, that might be the reason I get stuck each time
Okay listen those are for another puzzle!
Did you talk to Captain Kate, yet? She has something crucial!
The thing is you probably did all this now and forgot some earlier info by now that is important at this part, though!
I know, I’ve done it!
Er, I got Captain Kate arrested
That´s good actually! Now get her and her stuff out again!
But she’s soooo annoying…
Okay no more hints for nowsies.
Never mind, you need something she has. Remember where you got your stuff when you were in prison.
Ahaaaaa! 
The reason I´m outright telling you is that @RonGilbert has admitted that was a flaw of the game.
He kept saying during the development of Thimbleweed Park that you never should only get an important piece of information once. But should always able to get it again later when you need it. And there it wasn´t the case.
After you done all the spitting contest stuff and get all the alcohol you want, you have forgotten that you can ask Captain Kate for her near grog, as the barkeep won´t tell you that anymore.
So it looks like you put her into prison without knowing why and are surprised now by the content of her envelope. Yes, you definitly needed help there and it is not your fault!