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Settlers for me is like that one band you discovered in high school that no one else had heard of. Then all of a sudden everyone got into it and now they're not cool anymore. I discovered Settlers when my college roommate brought it back from Germany. We played it in German (with none of us speaking German except my roommate) and due to the game's simplicity, had no problems learning and playing.
Then it seemed like EVERYONE knew about Settlers and it started appearing in English. I started to lose interest mostly due to burnout. However, I also consider it to be my first hipster moment. Recently however, I've started to rediscover what it is that makes this game so popular.
Gameplay is simple yet strategically deep. The board is a random set of hexagons, each representing a particular resource. Numbers between 2-12 are assigned to each so the board is different every time you play. The objective is to obtain 10 victory points before anyone else (expansions raise this to 12). You gain points by building settlements, cities and roads. On a roll of a 7, the robber can shut down a tile and steal resources.
Trading resources is an encouraged, and certainly necessary part of the game. Resources can then spent to expand, or upgrade your settlements into cities. You can also purchase development cards which allow you to bump the robber, give you free roads or other improvements.
The rules are very simple. I was able to learn despite all the components being in German. This is a game you can get your non-gamer friends to play. There are three expansions for the game: Seafarers, Cities and Knights, and Traders and Barbarians. Each adds a new level of play. In Seafarers, most of the board is unknown and is revealed as you explore. In Cities and Knights, you must defend Catan against barbarians while improving your cities internally. I have not played Traders and Barbarians, but it allows movement on roads and various other scenarios.
The game supports 4 players, but also has a 5-6 player expansion (you'll need one for each further expansion, so it does get a bit pricey). For your first expansion I'd recommend Cities and Knights. Seafarers is good but Cities and Knights has a lot more depth. Learning this game is much less intimidating than Agricola or Dominion. If you've never played a Euro-style game before, this is a great place to start.