Once Upon A Time

How:

Cards, friends, minimal table or floor space.

What:

Story telling collaboration with surprise theft of narrative control and awesome ending phrases that each is trying to work towards.

Who:

Children, adults, and anyone who likes taking random, disparate elements and weaving them into a fairy tale style story.

Where:

Your friendly local game store, or Amazon has it ($24).

Why:

This one crosses all age groups, getting to our storytelling instincts very effectively. I played a ton of it in high school, and just recently recommended it to some older friends to bring along for a visit to some family with children. Kids get this quickly, adults can jump in easily, since the rules are light and the replayability very high. Plus it's small and portable.

Fallen London (aka Echo Bazaar), from Failbetter Games

(First, how awesome is Failbetter Games as a company name?)

I'm taking this in the order of "What am I playing right now?" so you'll hear about the things I play as I play them, if they are awesome enough that YOU should play them too. I'm also experimenting with my template, and would love feedback. If you're asking When? the answer is Now!

How:

Web browser, mouse only, mostly just text.

What:
Turn based, supernatural, narrative game with novel mechanics, long story arcs, and cooperative or competitive social interactions. Freemium in very good ways.

Who:
You should play this game if you like filling in narrative gaps and a deep story taken in small pieces. Play if you enjoy a casual yet long-term game, which you can pick up for 5 minutes throughout the day. Play to explore a novel, creative world that is spooky and funny and adventurous.

Where:
Online at Fallen London

Why:
Their storytelling mechanism allows you to fill in many details and interstitial gaps for your own character's narrative while giving you all kinds of fun choices to make. Rarely have games made me pause and think for a minute about my next action, but this one has multiple times.