The proper environment, engaging conversation starters and trustworthy company can help make adolescents feel comfortable enough to engage thoroughly in a conversation. The key is to make teens feel they're not being coerced into a boring and mandatory chore.
The Conversation Shaker
The Conversation Shaker is an iPhone application that gives all sorts of discussion topics and ice breakers simply by shaking the phone. Questions include ones that encourage lighthearted banter and making tough decisions. The app can be downloaded free at iTunes.
The Ungame offers hundreds of getting-to-know-you questions that teens and entire families can enjoy. Players can play the discussion-only version -- cards with icebreaker questions -- or the noncompetitive board game version. There is the Standard Ungame, the Christian Ungame and the Catholic Ungame, all three of which come in numerous versions. The official website of the game includes a link to 50 ways to use the game.
Table topics are a fun and pressure-free way to open up the lines of communication over time with a teen. Print out topics or discussion questions, cut them into strips, and place them in a decorative container in the center of the dinner table. Each night, family members take one of the topics or questions from the container and go around the table discussing or answering them. You never run out of topics, and it provides fresh dinnertime chat every evening. Jokes and riddles can also be used.
If card games are a bit too traditional to you, Thumball is a squishy alternative. The Thumball is a soft soccer-type ball in which each panel has a word, graphic, photo or logo connected to a specific topic printed on it. Catch the ball and respond to the panel under your thumb. The ball comes in 18 designs.