Script removes the last 2 indexes in a table but only 1 every other time?

I'm making a private message/notification system for fun. I have most everything down, but there is one bug I haven't been able to iron out. My system works like this: I type a command in the command bar which goes to a global function that takes a variable form the command and turns it into the text of a Message. That Message is put in the player object.

I just realized this is going to take a while to type, I'll just post the code and hope you understand it. If you need help deciphering my messy code just ask for an explanation.

player = game.Players.LocalPlayer
gui = player.PlayerGui["Messages"].TextLabel	
iu = false
waiting = {"Don't delete me ;_;"}
deb = false
deb2 = false
removable = true
function tweenin(text)
	iu = true
	gui.Text = text
	gui:TweenPosition(UDim2.new(0.25, 0, .125, 0), "Out", "Quad", 2, false)
end

function tweenout()
	gui:TweenPosition(UDim2.new(0.25, 0, -1, 0), "Out", "Quad", 2, false, function()
		iu = false
	end)
end

player.ChildAdded:connect(function(mes)
	if mes:IsA("Message") then
		print("Message recieved")
		if not iu then
			print("not iu")
			tweenin(mes.Text)
			gui.button.MouseButton1Click:connect(function()
				deb = true
				tweenout()
				mes:Destroy()
				wait(.5)
				deb = false
			end)
		else
			print("iu")
			table.insert(waiting, 1, mes.Text)
			repeat wait(1) until iu == false
			print(table.concat (waiting, ' '))
			print(waiting[1].." going")
			tweenin(waiting[1])	
			gui.button.MouseButton1Click:connect(function()
				deb2 = true				
				tweenout()
				if removable then
					print("removing") -- When it removes two things from the table this prints once, just like every other time.
					table.remove(waiting, 1) -- The only place that anything is ever removed from a table. 
					print("removed") -- same as above, only prints once
				end	
				removable = false
				mes:Destroy()
				repeat wait() until not iu
				wait(0.5)
				deb2 = false
				removable = true
			end)		
		end	
	end
end)

Here's the output:

Message recieved
not iu -- first message starts without having to wait
Message recieved
iu -- is waiting
Message recieved
iu -- is waiting
Message recieved
iu -- is waiting
Gold 300, Experiance 5, Level 1, Don't delete me ;_; -- list of waiting message
Gold 300 going -- is going to be next
removing -- whichever just went gets removed
removed
Experiance 5, Level 1, Don't delete me ;_;
Experiance 5 going
removing
removed
Level 1, Don't delete me ;_;
Level 1 going 
removing -- This only prints once, but the last index in the table (don't delete me) disappears without a trace....
removed

Thanks for any information you can give me, LightArceus

I have no idea how to fix what You made, because I don't actually see how that problem is produced.

EDIT: I answered with an answer for the question in the title by accident, that answer (the original answer)is below, in case it's ever any use.

local ot = false --define local variable ot as false

if ot == false and #table > 1 then --if ot is false and there's more than one object in the table
table.remove(table,-1) --remove last
table.remove(table,-1) --remove last again
ot = true --set ot to true
elseif #table == 1 or ot == true and #table > 1 then --but if there's only one item in the table, or ot  is true, and there's more
table.remove(table,-1) --remove the last object in the table
ot = false --set ot to false
end --end