Getting to know someone new is very much like venturing into unchartered territory without a map or compass of any kind to guide you. As a result, it is common to feel anxious or unusually nervous, which tends to only aggravate stress levels so that the odds of initiating or even maintaining a normal conversation are unlikely to work in your favor. There are a number of dating tools available today; self-help tidbits designed to provide you with a laundry list of possible conversation topics for you to experiment with on your next date. Some of these may be helpful but if used inappropriately, they could also backfire by making the discussion seem unnatural or rehearsed.

In order to maximize your potential for success, I would like to make a suggestion for how to get the conversation flowing naturally on your next date. Rather than try and force a dialogue with which your date may or may not be comfortable, consider inviting your date to play a game with you. The object of the game is, of course, to get to know more about each other, the method is your typical question-answer format, and the best part about it is that in the end, you both win.

Begin by acknowledging how nerve-wracking the process of getting to know someone new can often be. Let your date know that in anticipation of those dreaded uncomfortable silences for which first dates are so notorious, you have prepared a list of questions to help stimulate the conversation. The rules are simple: each person gets to choose a specific number of questions from the list (as many or as few as you feel comfortable with) and both people take turns answering the questions that their partner has chosen. If either you or your date feels uncomfortable about answering any of the questions, then you may choose to plead the fifth, at which time the person who asked the question would select a different one. The answers that are generated from the game or even the experience of playing the game itself can then be used as a foundation upon which to build more discussion.

Prior to your date, take some time to develop a list of questions that you can use for this activity. You could just randomly pick them from the Internet or even from this article but I would suggest using these ideas as mere guidelines by which you can formulate unique questions that are tailored to what you would most want to know about your date or vice versa.

Examples of possible questions:

• What is the most mischievous thing you’ve ever done?
  
  
• Do you ever remember your dreams?
  
  
• If money was not an issue and you could travel anywhere, where would you go?
  
  
• Describe the greatest personal challenge you’ve ever faced.
  
  
• What was your favorite toy as a child?
  
  
• If you could be anyone else for a day, who would you be and why?
  
  
• What is your biggest pet peeve?
  
  
• Describe the most adventurous thing you have done.
  
  
• What is the hardest habit you’ve ever had to break?
  
  
• If you could choose one super power, what would you choose and why?
  
  
• When is the last time you cried and why?
  
  
• What is your least favorite food?
  
  
• Where do you see yourself in five years?
  
  
• What was your favorite school lunch?
  
  
• Describe your best childhood memory.
  
  
• If you had the power to change one thing about the world, what would you change and why?
  
  
• Have you ever gone skinny dipping or streaking?
  
  
• What’s your favorite day of the week?
  
  
• Describe a time when you laughed until you cried.
  
  
• If you were going to be exiled on a deserted island, what 3 things would you want to have with you?