70 Dares to Ask Over Text to Get Closer to Your Crush

Texting your crush can be nerve-wracking, but it’s also a fantastic opportunity to get closer in a fun and playful way. This list of 70 dares to ask over text is designed to break the ice, deepen your connection, and add a spark of excitement to your digital conversations. Whether you’re just starting to get to know each other or looking to inject some fun into your ongoing chats, these dares will challenge both of you to be more open, daring, and engaging.

Get ready to transform your texting routine into an adventurous exchange that could lead to more heartfelt interactions.

Getting-to-Know-You Dares

Start your texting adventure with these light and playful dares that are perfect for breaking the ice. These questions are designed to uncover fun facts about your crush in an engaging way, setting a friendly and curious tone for your conversations.

1. Dare to send me a selfie of what you’re doing right now.
2. Send me the last song you listened to and tell me why you like it.
3. I dare you to text me using only emojis for the next 15 minutes.
4. Share the title of the last movie you watched and what you thought of it.
5. Send me a photo of your pet doing something cute or funny.
6. Text me a picture of something you cooked or ate today.
7. Dare to tell me about a hobby you have that most people don’t know about.
8. Send me a childhood photo and tell me a story about that day.
9. I dare you to describe your dream vacation in detail.
10. Share a picture of your favorite book or movie and explain why it’s your favorite.

Flirty Fun Dares

As you get more comfortable, these dares introduce a flirty twist to your texts, encouraging both of you to open up in more playful and teasing ways.

11. Dare to describe your first impression of me.
12. Send me a picture of your outfit today and let me guess where you were going.
13. I dare you to send me your best pickup line.
14. Text me three things you find attractive in a person.
15. Send a voice message saying something you like about me.
16. I dare you to share a secret that makes you smile.
17. Text me a hypothetical date scenario and ask me how I’d respond.
18. Send me a funny or flirty GIF that captures your mood right now.
19. I dare you to tell me something you’ve never told anyone before.
20. Ask me a bold question about my relationship goals.

Adventurous Challenges

These dares are designed to push the envelope slightly, encouraging bolder interactions that can deepen the connection and add an element of challenge and excitement to your texting dynamics.

21. Dare to plan a virtual date night and describe what we would do.
22. Send me a series of clues about something surprising about you, and let me guess.
23. I dare you to write a short, funny poem about how we met.
24. Send me a dare that you want me to complete.
25. I dare you to send a playlist of five songs that describe your personality.
26. Text me a photo of something you’re scared of and explain why.
27. Dare to tell me about a time you felt most adventurous.
28. Send a picture of something you treasure and tell me its story.
29. I dare you to describe a perfect day with someone special.
30. Challenge me to do something out of my comfort zone and document it for you.

Deep Connection Dares

These dares are aimed at fostering a deeper emotional connection, with questions and challenges that require thoughtfulness and vulnerability, setting the stage for more meaningful exchanges.

31. I dare you to share your biggest aspiration in life.
32. Send me a text expressing a personal challenge you’re facing.
33. Dare to describe a moment that changed your life.
34. Share a deep fear you have and how you manage it.
35. I dare you to tell me about a book or movie that deeply moved you and why.
36. Text me about someone you admire greatly and the reasons behind it.
37. Send me a confession about something you wish you could change about yourself.
38. I dare you to share an experience that taught you a valuable lesson.
39. Text me your thoughts on love and what it means to you.
40. Ask me a question that you feel could bring us closer.

Spontaneous and Quirky Dares

Inject some spontaneity and humor into your conversation with these quirky dares. They’re designed to add unpredictability to your interactions, making your text exchanges more lively and entertaining.

41. I dare you to send a funny voice note pretending to be a famous character.
42. Text me a made-up story using both our names.
43. Send a series of photos that tell a silly story from your day.
44. I dare you to invent a crazy holiday and describe how we would celebrate it.
45. Send me a doodle of us going on an adventure.
46. Text me a photo of the weirdest object you have in your room and tell me its story.
47. I dare you to make up a ridiculous law that everyone should follow.
48. Send me a photo of your funniest face.
49. I dare you to describe your day in the most dramatic way possible.
50. Ask me the most bizarre question you can think of.

Bold and Intimate Dares

As you grow more comfortable with each other, these dares delve into more intimate and bold territory, encouraging both vulnerability and a deeper sense of closeness.

51. I dare you to tell me about a moment you felt truly loved.
52. Send me a text detailing a moment you felt proud of yourself.
53. I dare you to share your feelings about our conversations so far.
54. Text me something you look forward to in a relationship.
55. I dare you to describe how you feel right now using only song lyrics.
56. Send me a list of things that make you feel peaceful.
57. I dare you to tell me about a dream you had that included me.
58. Ask me something you’ve always wondered but felt too shy to ask.
59. I dare you to tell me about a personal achievement that you rarely talk about.
60. Text me your thoughts on what trust means in a relationship.

Reflective and Future-Oriented Dares

These dares focus on reflections and future aspirations, helping both of you to share dreams and life goals, which can build a foundation for a potentially deeper relationship.

61. I dare you to describe where you see yourself in five years.
62. Send me three goals you’re working towards this year.
63. I dare you to share a place you want to visit and why it’s important to you.
64. Text me your idea of a perfect day from morning to night.
65. I dare you to tell me about a tradition you want to start.
66. Send me a description of your ideal home.
67. I dare you to share an experience you want to have before your next birthday.
68. Ask me about a life experience I want to share with someone special.
69. I dare you to envision our future conversation a year from now—what are we talking about?
70. Text me something you want to achieve together if we get closer.

These dares are crafted to not only entertain and intrigue but also to encourage meaningful connections that go beyond superficial interactions. Each set of dares progressively builds on the last, allowing you both to gradually open up and share more personal and intimate details as you get to know each other better.