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The Conversationalist Sensationalist: Conversation Starters

In my first post on the topic of conversation I write about approaches and mechanics of conversation, primarily centered on open and closed questions and understanding when and how to use them.  This post looks to expand on that topic and give you, the reader, some ammunition to help make those conversations better or, at least, a little less awkward.So start with thinking of questions that require an open response, questions that take thought and interpretation.

  • Ask your date what their  their worst job or even worst boss was. This is sure to stir up some good conversation and lend you some insight into how your date responds to negativity.  Take note if they remain bitter over it. It could indicate that they hold grudges, or even just seeing the forest through the trees…
  • What is one food you just can't live without? This is a fun one to ask as well, because you gain some insight into their tastes obviously.  A lot of times people will associate this question with childhood favorites, or is connected to a memory and that is yet another jumping off point by asking your date why they like the food they mentioned.
  • What's your weirdest habit? If your date makes an effort and actually answers this then that is a good sign that they are having fun.  If they don't choose to answer it they may be uncomfortable or a bit stuffy.  You can always offer your own answer to start and that can help ease tension, at your own expense.
  • If you won the lottery, what would you do with it? This question is fun, I think, because there's a lot of places you can take it.  If your date gives you a straight forward answer like taking care of the parents, buying a house and saving the rest, that's cool, but there's more fun to have with it.  Because of my sense of humor, I usually tend to err on the side of outlandishness.   I'd buy a nuclear powered slingshot water cannon, or a child launcher or a small army of pet komodo dragons.  I know.  I'm weird.
  • Your most terrifying moment. I like this question because it really does open things for a serious answer.  Also, it can give you insight into how your date views life and death as well as their spiritual inclinations.
  • What season do you most anticipate? I like this question because, certainly, somebody's got to have a time of the year that they prefer more than another.  Really, you get to kill two birds with one stone here.  You're able to dissect likes and dislikes the winter, you can comment on how that doesn't surprise you given their lack of a good tan… I mean, don't be a dick, but be playful.  My default setting is jerk, by the way.  That will get you slapped more often than not. I'm just saying.

The important thing here is to use these topics to get your date to open up, especially if you're not sure what to talk about.  Then, ideally, you can move on to another topic that either you or your date is more comfortable with.  Remember, people really do enjoy talking about themselves.  If they say otherwise, they're pants are most assuredly on fire.

Author profile

Alex is the founder and managing editor at the Urban Dater. Alex also runs: DigiSavvy, for which he is the co-founder and Principal. Alex has a lot on his mind. Will he ever get it right? If he does, he'll be sure to write.

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