How to ignite the conversation…

When I got back into the dating world, it was really hard not to sound like a broken record with each new date, repeating the same questions over and over. In fact, I went on a few speed dating events to help me change my poor dating skills. Everyone at the speed dating events were asking the same thing and no one was really connecting.

Speed DatingThe dreaded lame questions such as “Where are you from?”, “What do you like to do for fun?”, “How many siblings do you have?”, “What do you do for work?”, “What do you want to do as a career?”…throw these questions out as first date questions, please!!!

You want to take a genuine interest in someone but you do not want to ask “yes” or “no” questions that leave the conversation dry. Throw out simple questions that start with “Who”, “Where”, “How”, and sometimes “What”, and replace them with “tell me about”, or “describe”.

Guys: Avoid questions that make you sound pathetic. If the girl is on a date with you, she already liked something about you. She doesn’t need to hear negativity or comments that make her second guess her choice to be there such as “You’re so hot, so why are you single?”, or “Why does a girl like you need to be on Tinder/Match/eHarmony/speed dating/etc.?”. Also, practice what you may ask about. Don’t pull out a list of question or treat her like she’s on an interview!! Be casual and listen. Usually each answer can expand the conversation to other topics and experiences to share. Listen! And look, dear God, please try to look at her eyes when she talks!

Ladies: Men are not as familiar about holding an in-depth conversation as much as women. Generally, they don’t constantly talk to their friends about their feelings, fears, and goals in life like you do. The nicer, quieter, “better” guys for you don’t usually charm you as well as the experienced player. Give a guy a chance and get to know him back. Relationships are about both of you getting to know each other.

Here are a few great questions to help get the conversation going:

  1. Say you won a small lottery (like US $200,000). Besides giving to charity, tell me some things you would do with that money, in the first year?
  2. If you had a super power, what power would you have and how would you spend your life using this power?
  3. Complete the following sentence. There would be fewer divorces, if only _____.
  4. Tell me about your ideal family. And, is it similar to what you experience now or totally different?
  5. Tell me about how you enjoy to spend your Sundays (or, a “lazy day”).
  6. Describe your dream vacation, if time and money were not a factor.
  7. Was your major (form of study) what you wanted to pursue or would you do something else if you could do it over? Why?
  8. Describe something you’re superstitious about. Does it help you for a sporting event, work, life, or dating?
  9. Tell me about your life when you’re not working or dating; activities with groups and by yourself.
  10. Tell me about something you do that keeps you calm or makes you happy, even when you’re having a bad day.
  11. What’s one thing you wish you had known in college?
  12. Describe one extravagance (or “guilty pleasure”) you have for which you will never apologize.
  13. Which bill do you hate paying the most? and why?
  14. When it comes to love and relationships, what is the first lesson you want to teach your children?
  15. What is one day you would love to relive? (This will tell you something near and dear to their heart in a fun way)
  16. Bonus fun question: Ask them to give you two “truths” and a lie. Then try to guess which one is a lie.


Written by me.

14 thoughts on “How to ignite the conversation…

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    1. I think it’s a pretty reasonable question. I usually ask more ‘What do you do outside of work’. For me, I’m trying to work out, actually else they do with their life! It’s an important question!


      1. I guess it is a bit scripted, but then, so are many first date questions (ie. by definition, every question on this list).


  1. So more recently I’ve become much more ok with the ask the girl more questions about herself. Previously I’d been avoiding this – following the advice that ‘Don’t treat it like an interview’ and ‘Project yourself as awesome (by talking about something great you do)’. I think the reality is, most people enjoy talking about themselves, and so asking about themselves is a pretty straight forward way of generating a feeling of connection.

    Liked by 1 person

  2. I like bonus question 16! I’m definitely using that on my next date 😀
    and yeah speeddates can be the same… Went to a speeddate where they had 20 guys and 20 girls… All the conversations where the same… Except for one fun conversation… 😉

    Liked by 1 person

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