The First Date Question Game

First Date

So you’ve finally scored that first date with some lucky lady. Now you’ve got to figure out what you could ask so that the conversation is flowing smoothly. Well, there are so many different questions that you could ask! One golden rule that you should always adhere to is to ask open ended questions. You don’t want to ask a question that can be answered with a simple yes or no. By asking an open ended question, it will be the opening to an engaging (hopefully) conversation that will last for hours.


Here are some thought provoking questions that are great conversation starters.


  • What makes you smile?
  • What is the hardest habit you’ve tried to break?
  • Describe your favorite childhood memory.
  • What is the most exciting thing you’ve ever done?
  • If you could have a super power, what would it be?
  • What is one piece of advice would you give to yourself on your 18th birthday?
  • What is your favorite art form (or artist)?


These questions are only a few of the possibilities that you could ask that would create an engaging conversation. The key is to ask a question that you could answer too. You don’t want to ask her about art if you have no opinions on the subject matter.


When you ask any open ended question, you’re showing that you’re interested in what she has to say. Keep in mind that you don’t want to fire off questions like it’s the Grand Inquisition. The whole point of asking these questions is that the conversation flows easily. When she answers the question, respond, keep the conversation go.


If you ask what her favorite artist is, that could transition into possible exhibits that she’s been to, what galleries she’s visited, if she has any pieces of art in her own collection, and so forth. When there is a lull in the conversation, feel free to ask a question that would come naturally. If you asked about art and there is a lull, you don’t want to talk about something completely out of the blue like her work-out routine. You want the conversation to flow from each topic almost seamlessly.


Some topics that you should always steer away from on the first date are:


  • Past relationships and exes
  • Political affiliation and/or views regarding political issues
  • Religion
  • Sexual topics unless the conversation goes that way naturally
  • Financial status
  • Anything that may indicate you’re expecting a long term relationship right off the bat
  • Anything that is too personal regarding their body or appearance


These questions are okay to ask further down the road in the relationship. Some of these topics will come up in a general conversation, but you don’t want to ask them on the first date. Some of the things aren’t anyone’s business, especially someone who you’re just getting to know. It would be wise to stick to neutral questions that aren’t too invasive into their private lives. is a worldwide online dating site. For more dating advice and tips, visit

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