60 Dares to Ask a Guy Over Text to See If He’s Really Into You

Testing the waters with someone new can be both exciting and nerve-wracking. This list of 60 dares, crafted for text messaging, offers a playful way to see if he’s really into you. Each dare is designed to be light-hearted yet revealing, allowing you to understand his feelings better while keeping the conversation engaging.

Whether you’re in the early stages of dating or just curious about where things stand, these dares will add a fun twist to your chats and might just bring you closer together.

Light and Playful Teasers

Kick off the conversation with these easygoing dares that are perfect for testing the waters. These light-hearted challenges are designed to see how he responds to a bit of fun and playfulness, setting a cheerful tone for your exchange.

1. Dare you to send me the funniest meme you have on your phone right now.
2. Text me your cheesiest pick-up line.
3. I dare you to describe your day in only three emojis.
4. Send me a selfie with the weirdest face you can make.
5. I dare you to tell me your secret superhero name and why.
6. Text me three facts about yourself; one of them should be a lie.
7. I dare you to send me the last song you listened to.
8. Send a picture of what you’re wearing right now.
9. Dare to tell me the silliest thing you have ever believed.
10. I dare you to write a haiku about your lunch.

Flirty Challenges

These dares turn up the heat a little, inviting flirtation and a deeper exploration of his feelings for you. Engaging in these can help you gauge his interest through his willingness to participate and the nature of his responses.

11. I dare you to text me something you like about me.
12. Send me a flirty GIF that best describes your feelings for me.
13. I dare you to tell me about your first impression of me.
14. Dare to describe our first date using only movie titles.
15. I dare you to tell me something you’ve noticed about me but never mentioned.
16. Text me a picture of something that reminds you of me.
17. I dare you to tell me the most romantic place you’d like to visit.
18. Send me your best selfie and caption it from my perspective.
19. I dare you to describe a perfect day with someone special.
20. Dare to guess my favorite movie, and I’ll tell you if you’re right or wrong.

Deep Connection Dares

When you’re ready to delve deeper into his feelings and intentions, these dares will help you uncover more about his thoughts and emotions regarding you and your relationship.

21. I dare you to tell me about a dream you had that included me.
22. Send me a text describing your feelings about us in one word.
23. I dare you to tell me something you find challenging about relationships.
24. Text me a question you’ve always wanted to ask me but felt too shy.
25. I dare you to share a personal story that made you who you are today.
26. Dare to tell me your thoughts on love and relationships.
27. Send me a list of three things that make a relationship great, according to you.
28. I dare you to tell me about a moment when you felt really proud of yourself.
29. Ask me something you think will bring us closer.
30. I dare you to share your aspirations for our relationship.

Bold Revelations

These dares are designed for when you feel comfortable enough to push the boundaries further. They encourage openness and can lead to significant insights into his commitment and depth of feeling.

31. I dare you to describe what our future together could look like.
32. Send me a message about what attracts you to someone emotionally.
33. I dare you to share a fear you have about being in a relationship.
34. Tell me about a habit you have that most people don’t know about.
35. I dare you to share what makes you feel most connected to someone.
36. Text me about something you would change about dating today.
37. Dare to tell me if you believe in soul mates and why.
38. I dare you to share a change you’ve made for someone you cared about.
39. Send me a spontaneous message anytime tomorrow about what you’re doing at that moment.
40. I dare you to tell me something you think we should do together that we haven’t done yet.

Spicy and Suggestive Dares

When the mood feels right and you’re both comfortable, these spicier dares can add an intriguing element to your texts. They’re designed to elicit more suggestive responses and see how he handles a bit of steamy conversation.

41. I dare you to tell me about your biggest turn-on.
42. Send me a fantasy you’ve always wanted to try.
43. I dare you to describe how you feel about me using only sensual words.
44. Text me what you’d do if I kissed you right now.
45. I dare you to send a voice message saying something you’d whisper in my ear.
46. Send a playful or suggestive photo with a caption that teases.
47. I dare you to write a flirty message that could make me blush.
48. Tell me something you’d love to do on a date that we haven’t tried yet.
49. I dare you to share your thoughts on what makes someone a great kisser.
50. Text me a song that you think would be perfect for us to dance to closely.

Testing Commitment Dares

These dares are designed to subtly test his commitment and interest in taking things further, offering insights into his long-term intentions without making the conversation too heavy.

51. I dare you to tell me where you see yourself five years from now and if you picture us together.
52. Send me something you’d like us to do together next year.
53. I dare you to share how you’d handle a disagreement in a relationship.
54. Tell me about a relationship deal breaker for you.
55. I dare you to describe your perfect day, and see if it includes me.
56. Send me an idea for a getaway that you think would be perfect for us.
57. I dare you to tell me about a sacrifice you’d make for love.
58. Ask me a deep question that you feel could define our future.
59. I dare you to share your feelings about moving in with someone.
60. Text me your thoughts on commitment and what it means to you.

These final sets of dares are crafted to not only spice up your text exchanges but also to delve deeper into emotional territories that can help solidify your connection. Each dare challenges him to open up a bit more, showing his true feelings and how much he values your relationship.

Understanding His Responses

The way he responds to these dares can tell you a lot about his feelings and his comfort level with deeper engagement. It’s important to pay attention not just to what he says, but how he says it. Does he engage enthusiastically, or does he shy away from more revealing questions? His reactions can give you clues about his personality, his interest in you, and his readiness for a serious relationship.

If he jumps at the chance to share personal details and seems to enjoy these playful exchanges, it’s likely a sign that he’s genuinely into you and comfortable with where things might be heading. On the other hand, if he often hesitates or avoids answering, it might indicate that he’s either not ready for a deeper connection or perhaps not as interested as you are.

Use this opportunity to gauge where he stands and what his answers might mean for your future together. Remember, communication in a relationship is a two-way street; it’s about sharing and understanding each other’s feelings. So, while you learn about him through these dares, let him learn about you too through your reactions and responses.