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Get to Know Your Date with These Revealing Conversation Starters

Go from first date zero to second date hero with a little bit of homework
Go from first date zero to second date hero with a little bit of homework

Did you know that the saying ‘fail to prepare, prepare to fail’ can be applied to your dating life? Making sure you leave some time to do your homework before you step out on a first date will turn you from first date zero to second date hero.


Small talk on dates is fine, but if you want to ascertain whether you see your date again, find out if you have anything in common or you want to really delve into their character, you need to have some conversation starters up your sleeve.

The Safe Bets

These 8 questions are safe bets - the types of questions that reveal what someone does to while the day away in their down time, along with some quirkier questions to put a smile on their face. If your date reciprocates the question, it’s a good move to practise your response in advance so the conversation flows nicely.

  • What are your hobbies?
  • What are your favourite foods?
  • What makes you laugh?
  • What’s your favourite way to waste time?
  • Where is the most beautiful place near you?
  • What is your guilty pleasure?
  • What food do you know you shouldn’t eat but can’t help yourself?
  • What weird or useless talent do you have?

That’s Entertainment

If you gauged that your date likes to read, eat out or watch movies, some of these questions are interesting conversation savers. Making sure you’re listening to your date’s response will ensure you look interested in what they’re saying.

  • Do you prefer books or movies?
  • What was the last movie you watched?
  • Who is your favourite entertainer (i.e. Actor, Comedian etc)?
  • What was the last book you read?
  • Do you like to watch any sports?
  • Do you like to play any sports?
  • What restaurant do you eat at most?


Not everyone has travelled extensively, but these questions will help you ascertain that.

  • Have you travelled to any different countries?
  • Where is the most beautiful place you have been?
  • Do you prefer traveling alone or with a group?
  • Where would you like to travel next?

Keeping It Real

On a first date, it’s a good idea to keep the conversation light, not divulging too many personal details at this stage. The following questions will give a little insight into your date’s character, and hopefully enough to understand if you like the person enough to consider seeing them again.

  • What do you do to get rid of stress?
  • Who in your life brings you the most joy?
  • What song always puts you in a good mood?

Turn Offs

Getting negative on a first date is a huge turn off, but these two questions, if asked at the right moment, will give you some real insight into the things to steer clear of if you see the person again.

  • What is the most annoying habit someone can have?
  • What foods do you absolutely hate?

A Goal Without A Plan Is Just A Wish

Finding out someone’s goals is a great way of figuring out a person’s drive in life.

  • What do you want to accomplish before you die?
  • What are your goals for the next two years?
  • What do you want to do when you retire?

The Good Times

The past is always a tricky subject, especially if someone has had a troubled life. These light and breezy topics are fun to discuss, and are sure to open up the conversation no end.

  • What cartoons did you watch as a child?
  • Who were your favourite band or musician when you were younger? Do you still like them?
  • Who has had the biggest impact on the person you have become?
  • How have your goals changed over your life?
  • Which day of your life would you choose to relive?
  • What are the highest and lowest points of your life?
  • Whose advice do you always listen to?

Fantasies (Not that kind of fantasy!)

These are the kind of questions where you not only fantasise about something fun, but you find out what is important to your date, especially the lottery one!

  • What would you do if you won the lottery?
  • If you could only have one thing to eat, and one thing to drink for the rest of your life, what would they be?
  • What would be your perfect weekend?
  • If time froze for everyone but you for one day. What would you do?
  • If you were invisible for the day, where would you go?
  • If you could have a one hour conversation with anyone, dead or alive, who would it be?
  • Would you like to live forever?
  • What product would you stockpile if you found out it was being discontinued?
  • Who would be the best person to be stuck in an elevator with?

First Date No Nos

Julie Edelman, a dating advice guru for a leading mature dating website, explains some first date conversation no-nos in this fun dating advice video.


Ready for your date?

If you want to really get to know your date without getting too deep, bookmark this article in preparation for your next date and let me know how you get on. Good luck!

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