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Random, Interesting "Get to Know You" Questions to Ask on a Date

Updated on December 26, 2014

Dating is often an awkward process. Both parties don't know the other person well enough to be completely comfortable, yet an awkward date may result in the inability to get a second chance with someone they are really interested in. Both parties could potentially miss out on a great opportunity to get to know someone and, possibly, a great relationship.

A successful date results in an invitation to go out again. It's difficult to get to know who a person on a deeper level until you spend more time with them. The lack of a follow-up date invitation means that either they perceived the date as awkward or they have quickly stereotyped you, in which case it may be their loss.

One way to become more comfortable with your date is to do an activity before dinner or drinks. You may end up having a blast, in which case the date will be less awkward because impressions have already been made, and it will give you something to talk about at dinner.

I have created a list of random, but interesting questions you can ask someone on a first date. In my experience, if you can break the ice, the date goes a lot more smoothly. Often, an "icebreaker" question will turn into a deeper discussion. People don't usually give one-word responses! Before your next date, simply review the "ice breaker" list for ideas. You can use these questions or use them as a basis on which to to elaborate further. Have fun!

Random Questions

1) Do you have pets?

2) What's your favorite type of cuisine?

3) What's your favorite soft drink?

4) What's your favorite book?

5) What's the most interesting thing you have ever done?

6) What's your favorite holiday?

7) If you could do anything, what would it be?

8) What is your favorite television show?

9) What is your favorite movie?

10) What's your favorite hobby?

11) What's your favorite color?

12) What is your most amazing moment so far?

13) Who is your favorite actor or actress?

14) Who's your favorite group or band?

15) What's your favorite music genre?

16) What's your favorite car?

17) What do you do for fun?

18) What is your favorite hobby?

19) Do you like to travel?

20) What is your favorite place you have been?

21) If you could go back in time, would you change anything?

22) Who is your favorite historical figure?

23) What is you favorite school subject?

24) What is you favorite game show?

25) What is your favorite board game?

26) What is your favorite sport?

27) Who's your favorite sports teams?

28) Do you prefer the beach or the mountains?

29) What is your favorite song?

30) Who's your favorite author?

31) How many states have you visited?

32) How many countries have you visited?


33) What's your favorite flower?

34) What's your favorite season?

35) Had you rather be cold or hot?

36) What's your best memory?

37) When you were a child, what did you want to be when you grew up?

38) What was your favorite toy?

39) If you could vacation anywhere, where would you want to go?

40) Do you speak any other languages?

41) What's your favorite animal?

42) Who is your role model?

43) Who is your favorite celebrity?

44) Would you rather read a book or go to a movie?

45) What's your favorite restaurant?

46) If you could live anywhere, where would it be?

47) If you could meet anyone, who would it be?

48) What is the worst trend you remember?

49) Do you prefer to be indoors or outdoors?

50) Would you like to go out again?

Try to find the happy median between coming across as shy and coming on too strong. Using "ice breakers" should help you be more open, but don't bombard your date with too much on one date. Save some for the next time. Also, remember that, if your date should fail to go smoothly, you are dateable and there are plenty of fish in the sea. Sometimes, both people can do everything right and there is just no "connection". That's okay. It isn't anyone's fault and you just try again with someone else. It will happen with the right person and they will be worth the wait.

Whatever you do, be yourself, relax and have fun. When you are yourself, you will likely be at your most comfortable. This will help you relax. When you relax, you allow yourself the ability to have fun!

Do you find dating awkward?

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