What was your most embarrassing hobby in your childhood


Small talk is part of getting to know each other. But what if all topics about where you live, work, friends, pets and hobbies are exhausted? Then it can happen that there is an uncomfortable silence. In order to get back into a relaxed conversation from this situation, we have listed a few creative questions for you to get to know. Interesting questions can be the perfect support during the conversation and may give you new food for thought for other topics.

Sometimes it makes sense to ask for a superlative, the craziest, the dearest, the most beautiful, etc. But it is often difficult to decide which of the many experiences is the strongest. So simply ask the question again by giving it a time frame, for example: What was your best experience in the last year?

Don't make the mistake of memorizing this list of questions and just focusing on it. The best questions and topics arise from the situation - where you are right now, what you are doing, what is happening around you or, if a topic has been raised, to take it up and ask more precisely.

Use this list as a stepping stone and find connecting points from the answers you receive.

For example: 1. Question from the list
You: "What do you like to cook best?"
He: “I really like sauerbraten with dumplings. I learned that from my grandma. It is probably the only home-made meal that I can cook well, but I rarely get to it in my small kitchen. "

It now has several points of contact:
"Did you often go to see your grandma in the past? Where does she come from?"
"How is it that you just memorized the dish?"
“Well, that fits well. I have a big kitchen! Would you cook with me one day? "

If someone asks you, feel free to provide a little more details than necessary. In the example above, the answer "I like to cook sauerbraten with dumplings" would have been sufficient. But then the conversation would soon have come to a standstill.
So remember: Your interlocutor, like you, is looking for points of contact. Make it easy for him / her. Find a balance of details around the answer. Don't be too taciturn, but don't monologue either.
Listen carefully to your counterpart and make a note of the answers to your questions. Maybe it will spark and you can shine at the second meeting with “running gags” or re-exploring different topics.

Now we want to give you our list on the way:


  1. What was the most embarrassing moment in your life?
  2. What was your best vacation experience?
  3. Are you particularly proud of yourself?
  4. What was your best birthday present?
  5. Do you go to church on Easter / Christmas?
  6. How do you feel about faith
  7. Are you here by car? How was your driving test back then?
  8. Have you tried online dating before?
  9. What was the crazy thing that happened to you?
  10. What have you already experienced crazy?
  11. Who taught you to ride a bike?
  12. Have you ever done a skydive? (would you like to?)
  13. What was the funniest moment this year?
  14. How long have you known your best friends?
  15. Have you ever had a completely different look?
  16. What was your biggest fashion sin when you were young?
  17. When was the last time you went camping?


  1. Do you tend to follow your head or your feelings?
  2. Do you like to let off steam artistically / creatively?
  3. What do you do when you are bored sometimes?
  4. Can you dance / sing / make music / paint (or what you like to do yourself)?
  5. Do you know your unusual hobby or area of ​​interest? (If yes, talk shop or if no, explain it briefly
  6. I saw you were from ...
    1. Do you know any dialects
    2. How / why did you come to Dresden?
  7. What do you like to cook?
  8. Do you prefer a beach vacation or city trips?
  9. What always makes you laugh?
  10. What do you like to do on a Friday evening after work?
  11. What is your star sign? Maybe you are familiar with it and can guess a few traits.
  12. What do you do to make a good impression on a first date?
  13. Who is a role model for you? What inspires you about them?
  14. If your best friends would describe you, what two qualities
  15. would anyone call? (already quite personally so only later in conversation)
  16. Are you more of an early bird or a real morning grouch?
  17. What can you really get excited about?
  18. Do you have any hidden talents?
  19. What do you like to save for?
  20. Would you rather live in the city or in the country?
  21. What's your morning routine?
  22. How did you find out that Santa Claus / Christ Child does not exist?


  1. What else is at the top of your bucket list?
    (What else do you want to learn, experience, visit ...)
  2. What do you really want to do next weekend?
  3. What job would you have if you weren't financially dependent on it?
  4. Which country would you most like to visit and why?


  1. What's the funniest joke you know
  2. Which film makes you laugh / which one makes you cry?
  3. Do you have a favourite movie?
  4. Did you read an interesting book recently?
  5. What was the biggest faux pas you stepped into?
  6. What is your favorite place in Dresden or Saxony?
  7. Or questions like favorite hiking trail, favorite view, favorite café / restaurant
    And immediately afterwards the question, what makes this place so special for you?
  8. Do you have or have any pets? What was your favorite pet?
  9. Who is your childhood hero
  10. Who is your favorite star
  11. Do you prefer to drink beer or wine? (may I invite you to do it once?)
  12. Are you more of a coffee or tea drinker? (may I invite you to do it once?)
  13. Do you prefer to eat sweet or savory in the morning?
  14. What kind of hobby do you have?
  15. What did you write on your card during the introductory game? (chop again here, e.g. what is important to you or what has just let you travel to ...)
  16. Fascinating What the hiking guide said, did you know that? What did they think of doing it like that? or similar questions to stay on topic.
  17. Is the glass half empty or half full for you?
  18. How do you know date outdoors
  19. Have you hitchhiked before? (where or would you dare to go?)
  20. What are you reading at the moment?
  21. If you won $ 10,000 overnight, what would you do with it?
  22. You have the choice between three magical powers: invisibility, flying or stopping time, what do you choose?
  23. What is your favorite season and why?
  24. What is your favorite type of ice cream? (do we want to eat them together after the hike? (if in summer))
  25. Do you like to be out and about? What do you like to do when you are outside?

We wish you a lot of fun and success trying out our questions and look forward to reading your experience in the comments!

Lovely wishes,
Your outdoor date team