Are you planning on dating soon? Or are you already dating? Are you often finding dating uninteresting or dull due to many first dates being awkward and difficult for you and your date to open up?

Don’t worry, you are not the only one who feels that way. First dates can be difficult because it’s most likely that you and your date never met each other before your first date, especially if you are dating through dating apps or online dating. 

I have had a fair share of awkward, dull and exhausting dates as well, especially when I was fairly new to dating, I would cut the date short. For example, a while ago, when me and my date planned a dinner and a movie for our first date, I cut the date short by skipping the movie that night and going home directly after dinner. I made that decision back then because the dinner part of the date was very awkward and dull. 

Don’t get me wrong, my date was a lovely person, but both of us just did not know how to have a fun and interesting conversation. Of course there were the usual questions such as “what do you do for work?”, and “how do you spend your free time?”, but these questions usually led to shorter conversations, so that gave us more time for awkward silence during the night, which made me cut the date short without a second date.

There are so many questions you and your date could ask each other to get to know them better. Of course, you are also allowed to ask simple and basic questions like I did on my date, it helps you understand your date, and it helps your date understand you. However, more interesting, niche, and fun questions can really help you understand each other’s characters on a deeper level, not only that, but it can reveal both of your interests and hobbies and lead to longer conversations making the date more fun and light-hearted!

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First a cute gift idea

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Interesting date questions can play a significant role in reducing the embarrassment between the two people. Similarly, giving each other Custom Lapel Pins as gifts can also be a great way to promote the relationship between the two.

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A custom pin is a unique and personal item. When one gives a customized pin to the other, it shows that they have put thought into the gift and that they have considered the recipient's interests and the special bond they share. This small yet meaningful gesture can make the recipient feel special and valued, and it can strengthen the emotional connection between the two, thus promoting a deeper and more intimate relationship.

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What Are Some Fun Questions To Ask On A Date?

There are so many questions you can ask on your first date, but we picked out some fun and interesting questions you and your date could ask each other and respond to! Before you get into it, it’s also important to remember that you do not have to ask these exact questions. You are allowed to change them however you want, and it really depends on where the conversation is going between you and your date. The purpose of this list is to also give you ideas for questions to make your date fun and interesting!

31 Funny Date Questions

1. If you could have dinner with any fictional character, who would it be and why?
2. What are the 3 most ridiculous things you would want in your dream house?
3. What's your go-to karaoke song, and are you bold enough to sing a bit of your go-to karaoke song right now?
4. Can you try guessing 3 things about me right now? I’ll tell you if you are right or wrong.
5. What’s your guilty pleasure song?
6. What’s a meal you would consider as your favorite meal?
7. Who are your top 5 celebrity crushes?
8. Which historical era would you want to live in?
9. Would you travel backwards or forwards in time, and why?
10. If you were a superhero, what would your superpower be, and what would be your superhero name and can you tell me a bit about your superhero story?
11. What’s a song you always fall back on listening to?
12. Who were your top played artists this/last year on your Spotify?
13. What's the most unusual or interesting talent you have?
14. What’s your version of a girl dinner?
15. If you could have any animal as a pet (and it would be perfectly trained), what would it be?
16. If I never told you my name, what would you think my name would be?
17. What’s the most unhinged thing you’ve done on a date before?
18. If you could only eat one cuisine for the rest of your life, what would it be? 
19. What's the most impulsive thing you've ever done?
20. If you were stranded on a deserted island and could only bring three possessions, what would they be?
21. What childhood TV show or cartoon do you consider your favorite growing up?
22. If you could switch lives with any celebrity for a day, who would it be and why?
23. What's the weirdest food combination you enjoy?
24. What is your opinion on movie sequels?
25. If you think movie sequels are better, then can you name 3 movies with better sequels?
26. If you think movie sequels are bad, then can you name 3 movies with really bad sequels?
27. What's your guilty pleasure movie or TV show?
28. What’s something you do to relax after a busy day or a busy week?
29. If you were given a million dollars but could only spend it in one day, how would you spend it?
30. Which movie or tv trope would you be?
31. What do you think your role in a dystopian society would be?

What Are Some Good Flirty Questions To Ask On A First Date?

If you and your date are getting more comfortable and open with each other on the date, then you could make your first date more fun by showing a bit of intimacy and your romantic interest in them!

However, it is important to remember that you understand yours and your date’s individual comfort levels. If they show any sign of discomfort to these questions, then you can always go back to asking them less intimate and flirty questions listed above.

Good Flirty Question To Ask On A Date

32. Can you tell me about the first and the last time that someone made you blush?
33. What's your idea of the perfect date, and would you let me plan it for us sometime?
34. What are you weirdly attracted to?
35. If you could have any superpower to make dating easier, what would it be?
36. What's the most adventurous or spontaneous thing you've ever done in the name of romance?
37. What is your love language?
38. What is the dorkiest thing about you?
39. What is the best compliment that you’ve ever received?
40. If we were characters in a romantic movie, how do you think our meet-cute would happen?
41. Do you believe in love at first sight, or should I walk by again?
42. If you were a dessert, what would you be, and why?
43. Can you tell me about your biggest date fail?
44. What's your favorite way to be flirted with?
45. Can you name 3 green flags that you look for in a partner?
46. If we were to go on a spontaneous weekend getaway, where would you want to go?
47. What's the most romantic gesture you've either done for someone or received?
48. If you could have a candlelit dinner with any historical figure, who would it be?
49. Are you more of a sunrise or sunset kind of person, and why?
50. If you could create the perfect playlist for a romantic evening, can you name 3 songs that would be on it?
51. In your opinion, what's the most attractive quality someone can have?
52. If you were to teach me one dance move right now, what would it be?
53. Where do you think the best spot for a second date should be?
54. What are your top 3 favorite romantic movies?
55. Has any of your previous first dates told you how absolutely gorgeous/handsome you are?
56. Can you name your favorite TV show couples?
57. What’s a song you love making out to or would love to make out to?
58. If we were a couple by this year’s Halloween, then what famous fictional or non-fictional couple do you think we should go as?
59. Can you pick 3 of your favorite fictional characters and tell me who would you rather kiss, kill, and marry?
60. What’s better? Breakup sex or makeup sex?

Some of my own dates have led to this point and it made things a lot easier that we always managed to go on a couple more dates after the first date! However, I always made sure to look at and understand the comfort level of my dates before asking these questions.

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About the Author

Ridhi Yemireddy is a Content Coordinator for the Couply app. Couply was created to help couples improve their relationships. Couply has over 300,000 words of relationship quizzes, questions, couples games and date ideas and helps over 400,000 people.

Ridhi is also a Psychology Student, and studying at University of Stirling.You can connect with Ridhi on Linkedin here and Instagram here.