55 Questions To Ask Your Crush That Won't Make You A Try Hard

When you are fascinated and intrigued by someone, you want to cast that first good impression on that person. You often wonder how to strike a conversation without sounding silly or desperate. Everyone is different and so are conversation preferences. When you have a crush on someone, you always want to let that person know about your feelings without sounding desperate or trying too hard. Flirting is often a subtle way of letting the other person know about your interest in them. You don't have to be direct initially as you might make the other person a tad too uncomfortable. Beating around the bush can also make you appear silly and the other person would lose all interest. So how do you say the right things on your first date? How do you cast that first good impression? How do you let the other person know that you are interested without being over-dramatic? Your questions need to be just perfect and meaningful initially. Well, here are some 55 questions that you should ask your crush that won't make you a try hard:

1. When was the last time you cried? 2. What is your worst habit? 3. What do you regret the most in life? 4. What do you aspire to become someday? 5. On which actress do you have a crush on? 6. What are you hiding from your parents? 7. Which is your favorite exotic travel destination? 8. Who knows you the best? 9. If you could time travel, which moment would you go back to? 10. If you could change one thing about your past, what would it be?

Asking such personal and meaningful questions strike a chord and the other person sees your genuine interest in them. You can see that all the questions are just put forward to know the other person better. They are not full of lust nor are they deeply personal. But to give you a peek into the character of your crush, they are enough. The questions mentioned above are a little off standard, but they do intrigue your crush. If you come up with boring and obvious questions like your favorite hobby and favorite color, it might put off your crush immediately. He will side cast you as boring whereas in reality you have much more interesting to talk about. You just did not know how to start the right way.

11. Which is the best book you have read recently? 12. Which is your favorite food? 13. Which is your best soap opera of all times? 14. What is your poison? 15. Where would you prefer to go for a holiday - a beach or the mountains? 16. Rom-com or action-adventure movies? 17. Favorite actress or actor. 18. Rock music or country classic? 19. Your idea of comfort? 20. Favorite weekend getaway.

Questions like these are more to know about your compatibility with your crush. These should be asked in and between some other serious discussions only to get a rough idea of the person you have a crush on so that next time you know what movie to call your crush or where to go with him for dinner. It just helps you get along on an easier note. If your crush hates rom-com movies and you take him for one, he might get really bored! Personal favorites help you know your compatibility levels so that you can plan outings together. It is not that only if you two have similar tastes, would you get along as opposites do attract. But it is better to know about your crush's choices and you can tell him yours so that he notices your thoughtfulness the next time you both plan something together.

21. How did you get so attractive? 22. How can a person like you be single? 23. What qualities do you look for in your girl? 24. Have you been working out? 25. What is your idea of an ideal date? 26. What did you first think of me when you first set your eyes on me? 27. Have you ever been to a nude beach? 28. What do you wear to bed? 29. What is your biggest turn on? 30. Boob fetish or butt fetish?

The questions above are both personal as well as flirty. They will let your crush see another side of your character. Often your character is defined by the kind of questions you ask someone. If your crush answers them as wonderfully as you put them across to him, it means he likes you asking such personal questions and also shows interest in you. However, if he becomes uncomfortable with such questions then perhaps it means that he is not ready for such an intimate relationship yet. He might see you as a friend and you should continue being friends with him and refrain from such intimate questions.

31. Describe yourself in three words. 32. Describe me in three words. 33. What is that one thing that you would want to change about me? 34. Do you like tattoos? 35. Have you ever tried bungee jumping or skydiving? 36. Have you ever had sex outdoors? 37. Would you prefer to make out or cuddle with your gf? 38. The most thrilling job you desire in the world? 39. Have you ever cheated on your previous girlfriend? 40. Which is the naughtiest thing you have ever said to anyone?

You and your crush can share light humor with these questions. They are fun questions and give you a deeper insight into the nature of your crush. If you are an adventurous person yourself, these questions can help you plan outings with your crush. Your initial questions to your crush should not be any dirty text messages. If you send him dirty text messages right in the beginning, he might think of you as a pervert. You should get into sexting only after you and your crush get deeper into the relationship.

41. Which was your worst date ever? 42. Which was your most embarrassing moment? 43. When did you lose your virginity? 44. Who was your first crush? 45. Have you ever been slapped by any girl? 46. Would you rather be invisible or have an x-ray vision? 47. Do you prefer girls, guys or both? 48. What are you best at? 49. Your favorite sex position? 50. Would you play a prank at someone?

Again with these funny questions, you strike a light chord with your crush, get to know him better and make the evening nice and enjoyable. It often gets awkward to start a conversation with your crush on your first date. You don't know what to talk about and neither do you want to appear serious or bored. It is best to ask questions on a first date to your crush rather than talk only about yourself. Choose your pick from the list above and see if your crush gets interested with a particular question. That is the way you can strike a conversation on a subject dear to your crush.

51. How about we go out sometime? You can ask this sweet little question to your crush when you see from his body language about his obvious interest in you. He might be waiting for you to ask him or must be really shy. 52. What do you think is my best feature? When your crush shows obvious sign of interest in you, perhaps, you could delve deeper by asking him such cute and romantic questions. The answer might make him blush and make your heart skip a beat! 53. Would you rather call me 'sexy' or 'smart'? Again, a sweet question which will tell you what your crush feels for you. You get a better perception of how he sees you and you will definitely love his answer regardless of whichever he chooses. 54. Do you like me as a friend or something more? The answer that you have been waiting for desperately. His answer will tell you about the future of your relationship. 55. Would you like to go out with me tonight? Does he accept your invitation or not? If yes, make it one of the most memorable dates of your life!

These are the final questions that you have been waiting to ask since a very long time. Do not hit on your crush immediately with such questions. You need to know a little bit about the person and his interest in you before you come up with such direct ones. Do not send dirty text messages in the beginning as they can tarnish your image and your hope of getting into a good relationship. When you start a new relationship you have to be very careful about the kind of questions you ask in the beginning so that you do not mess up. You have to ask the kind of questions which lets your crush know that you are interested in them in a subtle way. Sometimes, while conversing with your crush, it is obvious to have lulls in between. The list of questions above helps you keep the conversation going. It gets easy to jump from one topic to another and meanwhile knowing your crush better and better. Communication is the key to knowing someone. The more you talk to a person, the more you get to know him. Only after a couple of dates, a couple decides whether they want to pursue their relationship or not. It is important to talk a lot but talk right. It is a delicate phase when your relationship is just building. You have to put across apt questions not only to cast a first good impression of yours but also knowing your crush as best as you can in the first few meets. Sometimes, people send dirty text messages initially which will ruin their chances of getting into a good relationship. While dirty text messages are fun and thrilling when you get deeper into your relationship, there is a time and period for everything.