“What If” questions are a fun and engaging way to deepen your connection with your partner. They can lead to unexpected laughter, thought-provoking discussions, and even reveal things about each other that you never knew. Whether you’re on a road trip, having a cozy date night, or just looking to spice up your conversations, these questions will help bring you closer together.

So, grab your favorite snacks, snuggle up, and get ready for some fun, deep, and even a little wild “What If” questions.

Why “What If” Questions Are Great for Couples

✅ Encourages deep and meaningful conversations
✅ Brings a playful and imaginative vibe to your relationship
✅ Helps you understand each other’s thoughts, values, and dreams
✅ Perfect for date nights, road trips, or lazy Sundays
✅ Creates new memories and inside jokes

100 Unique “What If” Questions for Couples

Fun & Playful “What If” Questions

1. What if we could teleport anywhere in the world for dinner tonight—where would we go?
2. What if we woke up tomorrow in each other’s bodies—what’s the first thing you’d do?
3. What if we could time travel for one day—would we go to the past or the future?
4. What if we had to survive on a deserted island—who would handle what tasks?
5. What if we could swap lives with a celebrity for a week—who would you choose?
6. What if we had to come up with a secret handshake—what would it include?
7. What if we had to create our own couple’s theme song—what would the lyrics be?
8. What if we had to plan a heist together—what role would each of us play?
9. What if we had to live in a tiny house or an RV—could we handle it?
10. What if we could adopt any exotic animal as a pet—what would it be?

Deep & Thought-Provoking “What If” Questions

11. What if we had never met—how do you think our lives would be different?
12. What if we could erase one bad memory—would you do it?
13. What if one of us lost our memory—how would you remind me of our love?
14. What if we could only keep five things from our home—what would you pick?
15. What if we could live forever—would you want to?
16. What if we had to describe our love story in one sentence—what would it be?
17. What if we could relive our first date—would we do anything differently?
18. What if we had to take a break from technology for a month—how would we spend our time?
19. What if we could ask each other one question and get a 100% honest answer—what would it be?
20. What if we had to create a vision board for our relationship—what would be on it?

Adventure & Travel “What If” Questions

21. What if we could go on an all-expenses-paid vacation—where would we go?
22. What if we could live in any country for a year—where would we choose?
23. What if we had to take a cross-country road trip—what would be our first stop?
24. What if we could go back in time and experience one historical event—what would we pick?
25. What if we had to live off-the-grid in the mountains—how would we survive?
26. What if we could only visit five places in our lifetime—where would they be?
27. What if we had to travel for a year with only a backpack—what would you pack?
28. What if we got stranded on an island—who would go for help, and who would stay behind?
29. What if we had to move to a country where we don’t speak the language—how would we adjust?
30. What if we found a hidden treasure map—would we follow it?

Fantasy & Sci-Fi “What If” Questions

31. What if we woke up one day with superpowers—what would they be?
32. What if we discovered we were actually living in a simulation—what would we do?
33. What if we had to survive a zombie apocalypse—who would last longer?
34. What if we could live inside any movie or TV show—what would we pick?
35. What if aliens landed in our backyard—would we invite them in?
36. What if we could freeze time for a day—what would we do?
37. What if we had the power to read each other’s thoughts—would we want to?
38. What if we found a portal to another universe—would we step through?
39. What if we were the last two people on Earth—how would we rebuild?
40. What if we could become immortal but had to leave everything behind—would we?

Money & Career “What If” Questions

41. What if we won $10 million—what’s the first thing we’d do?
42. What if we had to start a business together—what would we do?
43. What if one of us got an amazing job in another country—would we move?
44. What if we had to switch careers for a year—what job would you want?
45. What if we had to live on a strict budget—how would we manage it?
46. What if we could retire today—what would we do with our time?
47. What if we could only spend money on experiences, not things—how would we live?
48. What if we had to work at the same company—how would that go?
49. What if we had to make money using only our hobbies—what would we do?
50. What if we had to live paycheck to paycheck for a year—how would we survive?

Relationship & Love “What If” Questions

51. What if we could redo our first kiss—would we change anything?
52. What if we had to take a one-year break from social media—would it change our relationship?
53. What if we had to write love letters to each other for a month—would we enjoy it?
54. What if we had to spend six months doing long-distance—how would we keep the spark alive?
55. What if we had to pick one thing we admire most about each other—what would it be?
56. What if we could go back to the moment we first met—would we recognize each other?
57. What if we had to create a new relationship tradition—what would it be?
58. What if we had to cook dinner together every night—who would take the lead?
59. What if we could only say “I love you” in creative ways—how would we do it?
60. What if we had to plan a dream date with no budget—what would we do?

Final Thoughts

Using these “What If” questions can help you and your partner connect, laugh, and dream together. Whether you’re playing a game, filling time on a long drive, or just want to learn more about each other, these questions will keep the conversation going.

Recommendations for Couples

If you love fun conversations and relationship-building activities, check out these great tools:

📖 The Couple’s Journal: 365 Questions for Deeper Connection
🎲 Our Moments: Couples Edition Card Game
📚 The 5 Love Languages by Gary Chapman

Which question surprised you the most? Let me know in the comments,