The Game of Life
The Game of Life, otherwise known as LIFE, was created in 1860 by Milton Bradley. The current, modern version was published about 100 years later. The basic rules of the game still apply to life today.
In LIFE players travel through their lives from the time they choose to work or go to college to the time they retire. Along the way each player gets a job, gets married, and even has children. While this may not sound all that exciting to an adult, to a teenager the prospect of taking on such responsibilities (if only in a game) is enticing, and while having fun teens will learn a little about the skills needed to successfully navigate through the actual game of life.
Monopoly
Monopoly is another old-fashioned game that's maintained its relevancy through the decades. In Monopoly, rather than focusing on your job and raising a family, you focus on managing your assets and controlling your finances. As any adult knows, these are important life skills. By buying and selling properties and building houses and hotels, teens can learn the ins and outs of basic business practices, while at the same time gaining some understanding of how hard it can be to survive financially in a cutthroat, capitalist society.
Payday
Payday is a board game in which players try to collect the most money by the end of the game. The length of the game is predetermined by the players, and spaces of the game represent days of the calendar.
Play entails moving spaces, picking up cards, paying dues for things like town elections, and even gambling. The quickly changing fortunes of the game and high stakes teaches teens to be cautious with the important decisions and helps them understand the importance of planning ahead and considering all possible contingencies.
Poker
Although people play poker for a variety of reasons, from making money to passing time, poker does have some valuable life lessons to offer teens. In poker you learn to read people and try to determine when they are telling the truth or bluffing. This teaches teens to be skeptical and look out for themselves. You also have to be good with your finances and make your bets carefully; this is a lot like managing finances in the real world. You also need to think quickly and make big decisions with confidence (or give away your hand). These are all skills that come in handy later in life.