You’ve been texting, flirting, maybe even FaceTiming.
You know their coffee order and maybe their dog’s name.
But now that it’s been two weeks of consistent talking, it’s the perfect moment to go deeper.
These 100 questions are designed for when things are still new — but you’re both curious about what’s next.
They’re fun, flirty, thoughtful, and honest without being too intense.
Perfect for:
- Late-night convos
- Long walks
- Chill date nights
- That “so… what are we” stage
Flirty & Fun Vibes (Questions)
1. What was your first impression of me — be honest?
2. When did you realize you liked talking to me?
3. What kind of texts do you low-key wait for from me?
4. Do you think we’d vibe in person the same way we do here?
5. What’s your favorite kind of compliment to get?
6. What’s one thing I’ve said that’s stuck in your head?
7. If we had a first date tomorrow, what would we do?
8. What emoji reminds you of me?
9. Do you re-read our texts sometimes?
10. What’s your love language — and how can I speak it?
11. Do you smile when my name pops up on your phone?
12. What’s one thing you’ve wanted to ask me but haven’t yet?
13. Do you think we’d have chemistry in real life?
14. If we had a playlist, what’s the first song on it?
15. What’s your flirting style — subtle or obvious?
16. What’s one thing I do (or say) that makes you feel special?
17. What would you nickname me if we were dating?
18. Have you imagined what kissing me would feel like?
19. What’s the best flirty message you’ve ever received — and do I beat it?
20. What’s your ideal “good morning” or “goodnight” text?
Getting to Know You Better (Questions)
21. What’s something small that makes you really happy?
22. What’s one value that’s super important to you in a relationship?
23. How do you usually spend your weekends?
24. Are you more of a texter or a phone call person?
25. What’s your go-to comfort movie or show?
26. What kind of childhood did you have — chill, wild, or somewhere in between?
27. What’s your emotional safe space?
28. Do you believe in soulmates or timing?
29. What’s your vibe when you’re in love — playful, soft, intense?
30. How do you usually handle conflict in relationships?
31. What’s your zodiac sign — and does it actually match your vibe?
32. What’s a random opinion you feel strongly about?
33. Are you more of a planner or “go with the flow” person?
34. What’s your biggest green flag in someone?
35. What do you wish more people understood about you?
36. What’s something people usually assume about you — and it’s wrong?
37. What’s something you’re working on in yourself right now?
38. When do you feel most confident or alive?
39. Do you believe relationships should be 50/50 or shift depending on the season?
40. What’s something you never get tired of talking about?
Romantic & Emotional Connection (Questions)
41. How do you know when you’re really into someone?
42. Have you ever had a relationship that changed how you see love?
43. What scares you most about falling for someone?
44. What excites you most about it?
45. When was the last time you felt truly seen by someone?
46. Do you think love should feel safe, exciting, or both?
47. What kind of connection are you hoping to build — something fun, serious, slow, intense?
48. How do you usually show affection — words, actions, touch, gifts, time?
49. What’s something you’re afraid to tell people early on?
50. What’s one romantic gesture you secretly wish someone would do for you?
51. When do you feel emotionally closest to someone — deep talks, shared silence, doing life together?
52. What kind of attention makes you feel the most loved?
53. How do you handle emotional vulnerability — ease into it or go all in?
54. What’s your biggest relationship lesson so far?
55. What’s something you’d never compromise on in love?
56. Do you believe in “right person, wrong time”?
57. Have you ever had a situationship that taught you something valuable?
58. What does emotional safety mean to you in a connection like this?
59. What are you hoping this could become — honestly?
60. If this keeps going well, how would you want it to feel in a month?
Playful, Weird & Unexpected (Questions)
61. What food would ruin a first date for you?
62. If we were characters in a movie, what would be our scene?
63. Would you survive a haunted house or scream the whole way through?
64. What’s your weirdest pet peeve?
65. What’s your “I know I’m annoying but I don’t care” habit?
66. What song do you low-key sing in the shower and would deny in public?
67. Would you rather fight a bear-sized duck or a duck-sized bear?
68. What’s your comfort junk food you always go back to?
69. If you could instantly master a random skill, what would it be?
70. Would your pet approve of me?
71. What’s the most random thing that makes you emotional?
72. Would you rather be loved loudly or softly?
73. What’s your go-to “I’m in a mood” song?
74. Have you ever had a crush on a fictional character — who?
75. What’s your most “I can’t believe I said that” moment?
76. If you could get a tattoo that disappears after a month, what would it be?
77. What’s something totally useless you’re really good at?
78. What would you cook me if you had to impress me with one meal?
79. If I dared you to send me a voice note right now, would you?
80. What would you name our duo if we were a band?
“What Are We Doing Here?” Soft Check-Ins (Questions)
81. Do you feel like this connection is going somewhere — or just fun for now?
82. Have I been clear enough about what I want?
83. Do you feel like you can be fully yourself around me?
84. Is there anything you’re unsure of between us so far?
85. Are you still talking to other people — or just feeling things out here?
86. What pace feels good to you — slow, fast, steady?
87. Is there something I said that made you feel closer — or unsure?
88. What are you hoping I want out of this?
89. Do you feel like our energy matches?
90. Have you caught feelings — or are they still growing?
91. If I pulled back a little, would you notice?
92. If I leaned in more, would that feel good or too much?
93. What’s one thing you need to feel safe as we keep talking?
94. What kind of effort makes you feel seen?
95. Do I seem emotionally available — or hard to read?
96. How do you feel after our conversations — more grounded, excited, confused?
97. Do you feel like you’re getting to know me or just a version of me?
98. What would make this feel even better or clearer right now?
99. Are we still aligned — or should we talk about where we’re at?
100. If this is something real, how would you want to keep showing up?
Final Words
You’re still getting to know each other.
It’s new. It’s fresh. Maybe a little flirty and a little confusing.
But questions like these?
They help you build clarity, trust, and connection — one honest answer at a time.
So ask gently.
Answer honestly.
And let the real connection grow.