Europa Universalis 3/4. Then you can be disappointed by anything that precedes.

I just found out Native Expansion mod for Mount&Blade: Warband is absolutely awesome!!

Those Black Knights are so badass!! They're taking over Calradia!!

I recently found an awesome game online that never gets old. It's called Diplomacy, I can send you a link to the site if you're interested!

Dark Knights*

Crusader Kings 2, better version of EU which is a better Civ

Nah, in CK2, being ruler of Europe is like fifty years' work. Plus, the character search interface offers too few filters - I realise that a real eleventh-century kings wouldn't have filters either, but they had advisors who were paid just for this sort of work. I find CK2 to be more work than challenge, I like the EU games better (especially the new EU4, it fixed all but one of my grievances with EU3DW).

Hydro - what were all those grievances? I haven't tried EU IV yet.

And do you want to stay in this genre of game or jump to a different genre? Because there's tons of stuff out there that is amazing.

Advanced Tactics Gold - really good game.

An inability to easily conquer (or even get CB on) small islands next to your land. (Now any two provinces that share a common seazone are adjacent.) The relations system being in a way that there are only +200, +100 and -200 relations. Cascading alliances. The unneccessarily complex technology cost curve, that ensures that small nations can keep up. The woefully outdated and abusable Centres of Trade system. The fact that some initially big nations can be balkanized to no bigger than 3-province minors, while others are not so unlucky. The fact that if you are big, you won't be ganged up on, because everyone is happy that they are not next. Related, the fact that if you hover on infamy limit times 0.999, nobody notices how you grew three times your size in ten years. Hell, even the fact that the start date, 1399.10.14 may as well be the single least important date in world history. The words "any day now". (The siege system didn't change, but now, you are informed of how it works, and how any given siege goes). The fact that the Japanese and Chinese AI aren't prepared for Divine Wind gameplay in their areas. The papal system is improved a lot, and now the three western Christian religions are pretty much balanced.

And these are only the big ones. With every dev diary (and I followed them religiously), some change that was made made me very happy.

I can only recommend EU4, even against the fear that I'll be called "just another fanboy".

Everything I have read about EU4 claims it runs terribly on a Mac - unfortunately that's what I've got. Any other suggestions? Big fan of Age of Empires but there aren't many like it for the Mac platform.

Maybe the Total War series? IDK how Mac-compatible that is.

Rome Total War is good.

Did you try the new map pack for Civ 5? Also you could try a new Civ (unless you've played them all). You could try something completely different and get the Marvel MMO. It's free to play and all that.

If you haven't spent a decent amount of time playing as the Iroquois in Civ 5, you haven't had the complete experience.

I'll second the call for Europa Universalis 4 and/or Crusader Kings 2.

It's hard to top those.

EU and CK are great titles, even though I always prefered Hearts of Iron and Victoria to those two. Rome Total War is great game as well. Cant miss with either of those.

Tried the Empire Total War demo a few years back, was very impressed, and am even more so by the titles that have come afterward, thinking about purchasing RomeTW 2.
EU though...
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shit's intense, thats all I really have to say. Over the summer, my supervisor introduced me to it, but I haven't played it since.