Anniversaries are a great time to look back on all the special moments you’ve shared with your partner.
When your relationship or marriage reaches a milestone, there are plenty of ways to spark a fun conversation.
Many couples who have been together for a long time feel like they already know everything about each other. But there’s still so much more to learn!
In this article, we’ve got up to 100 conversation starters to help you make the most of your anniversary.
Key Takeaways
- Some of the best conversation starters for anniversaries are questions that help you both look back on the past year.
- You can ask each other how you’ve both changed over the years. What challenges have you faced separately, and how have you both dealt with them as a couple?
- To make it more lively, talk about your favorite inside jokes and the best nicknames you’ve called each other.
Your anniversary is the perfect time to think about why you’re together.
Whether you’ve been married or in a serious relationship for 12 years or just 12 months, there’s always something new to learn about your partner.
It just takes a little time and creativity.
You can use any of the sentences in the list below to start that meaningful conversation.
List of the Best Anniversary Conversation Starters
1. I can’t believe it’s been 5 years already. What’s been your favorite memory from all the time we’ve spent together so far?
2. What’s the one moment from our relationship that always makes you smile when you think back on it?
3. Another year together! Time flies, huh? What’s one thing you’ve learned about me this year?
4. What was your first thought when we first met? I always think about that moment.
5. We’ve made it another year! What’s your favorite tradition we’ve started over time?
6. Looking back, do you remember the first date we went on? It feels like it was just yesterday!
7. What’s something you’re excited for in the next year of our relationship?
8. What’s something small that I do that always makes your day better?
9. Another year with you! If you could relive one special moment we’ve had, which one would it be?
10. What’s the best surprise I’ve ever given you on an anniversary or special occasion?
11. What’s the one thing that made you fall for me in the first place?
12. What do you think is the most important lesson we’ve learned as a couple so far?
13. Happy anniversary to the one I love! What’s one way you think we’ve grown since we first started dating?
14. It feels like time is flying by! Do you have a favorite trip or getaway we’ve taken together?
15. What’s one thing you’d still like to do or experience with me in the future?
16. So what do you think is the best thing about our relationship?
17. Is there one thing about our relationship that makes you feel proud?
18. If you could pick any song that best describes our journey together, which one would it be?
19. Tell me a silly moment we’ve shared that still makes you laugh?
20. What’s something that always makes you feel loved by me?
21. Here we are, another year together! Do you have a favorite thing we do on our anniversary every year?
22. If you could sum up our relationship in just one word, what would it be?
23. What’s one thing about me that you’ve always admired from the start?
24. What’s one thing you’ve always wanted to try together that we haven’t yet?
25. Tell me your favorite way to celebrate our love on a day like today?
Best Anniversary Conversation Starters for Deep Chats
26. Looking back, what do you think has been the most important thing we’ve learned about love together?
27. I’m curious—how do you think we’ve both changed since we started this journey together?”
28. What’s one thing about our relationship that makes you feel the most secure and loved?
29. Here’s to us! If you could describe the core of our relationship in one sentence, what would it be?
30. What’s a lesson our relationship has taught you that you didn’t expect to learn?
31. It’s been another amazing year together. What do you think has been our greatest strength as a couple?
32. So tell me something about our relationship that you’re proud to share with others?
33. Can you remember any moment in our relationship that felt like a turning point for you?
34. If we could go back and give our younger selves relationship advice, what would you say?
35. What’s one way you think we’ve grown as a team over the years?
36. I want you to tell me one dream or goal you have for us that we haven’t talked about yet?”
37. What’s one habit or ritual we have that makes our relationship feel special to you?
38. If you could relive one moment from our time together, which one would it be, and why?
39. What’s one thing you’ve learned about yourself through our relationship?”
40. If you could imagine our future together 10 years from now, what’s one thing you hope we’ll have achieved as a couple?
Best Anniversary Conversation Starters for Romance
41. So, how does it feel to still have the hottest partner around after all this time?
42. Another year together—tell me, do I still make your heart race like I used to?
43. What’s one thing I do that drives you absolutely wild, and do you want me to do it more often?
44. If you could plan a perfect, romantic night together, what would it look like?
45. Do you ever look at me and think, ‘Wow, I’m so lucky’? Because I do when I see you!
46. Another year with you! What’s one thing about me that still turns you on, even after all this time?
47. Be honest—did you know you’d still find me this irresistible after all these years?
48. If you had to pick one thing I do that makes you melt, what would it be?
49. What’s your favorite part of being with someone as good-looking as me?
50. We’ve been together for another year, but tell me—do I still know how to sweep you off your feet?
51. What’s one thing about me you think no one else will ever match?
52. What’s your favorite way for me to spoil you—and can I do it tonight?
53. Do you think we’re still as good at flirting with each other as we were when we first met?
54. What’s your favorite thing about the way I show you how much I desire you?
55. If we had the whole night to ourselves, just us two, what would you want to do?
Best Anniversary Conversation Starters for Future Plans
56. What’s one thing you’d love us to achieve together before our next anniversary?
57. Where do you see us living five years from now? Let’s talk about what kind of home or city would fit us best in the future and how we’d build our dream space together.
58. What’s a new tradition you’d like us to start this year? It could be something small like a weekly dinner theme or a big annual trip—something that’s just for us.
59. What’s a skill or hobby you think we could try learning together? It’d be fun to grow together in new ways. Don’t you think?
60. If we could take a month off next year, where would you want to go? Let’s talk about dream destinations.
61. What’s one personal goal I can support you with this coming year? I want to be part of helping you achieve something that’s really meaningful to you.
62. What’s something you think we can do to make our relationship even stronger? Let’s figure it out together.
63. How do you think we’ll celebrate our 10th anniversary?.
64. Let’s think of fresh and exciting things to do to keep our time together unique and enjoyable. What’s a fun or romantic date idea we haven’t tried yet?”
65. What’s one thing you’d love us to do more often as a couple? I want us to make time for what matters.
66. If we started a business or project together, what would it be?
67. What do you think our weekends will look like in a year? Would it be filled with more adventures, relaxing at home, or something completely different?
68. What’s a family tradition we could start for our future? Even if it’s just us for now, thinking about what we’d carry into the future is fun.
69. What’s one thing you want to save up for together? Let’s talk about how we’d make it happen.
70. If we wrote a bucket list for our relationship, what’s the first thing you’d want to add?
Best Anniversary Conversation Starters for Unresolved Conflicts
71. Be honest, Is there anything I’ve done recently that upsets you but we haven’t talked about yet? I’d love for us to clear the air and make sure nothing is quietly bothering you.
72. I want to make sure I’m showing you how much you matter to me. So are there things I do that sometimes make you feel misunderstood or unimportant?
73. Do you feel we’ve fully solved past arguments, or are there things we need to revisit?
74. Is there anything we’ve been avoiding discussing that you think we should address now? Let’s use this moment to talk openly about anything that might be lingering.
75. I want us to find healthier and more loving ways to work through tough moments. Let’s talk about how we can handle disagreements better in the future.
76. Are there moments you’ve felt like I didn’t listen to your feelings properly?
77. I’d love to know how I can do better when we’re not on the same page. So tell me if you do feel like I take your concerns seriously enough when we disagree?”
78. Have I ever done something that hurt you, but you didn’t know how to bring it up?
79. Today being our anniversary, I want to make sure even tough conversations bring us closer instead of apart. Do you think there’s something about how we argue that we can improve together?
80. Are there decisions we made in the past that you wish we handled differently?
81. I think this is the right moment to address things that might quietly bother you. Are there any habits of mine that you wish I could change but haven’t said before?
82. Have we fully forgiven each other for past mistakes, or do you think there’s still work to do?
83. I’d love to know if there’s a way I can make you feel more heard.
84. Is there a time I misunderstood you during an argument and didn’t give you a chance to explain?
85. Is there something you’ve been holding back because you’re worried about how I’ll react? I want you to feel safe sharing anything with me, no matter how hard it feels.
Best Anniversary Conversation Starters for Fun and Laughs
86. What’s the funniest thing I’ve done this year that still makes you laugh? Let’s relive that moment—I promise not to get embarrassed!
87. If we were in a reality show about our relationship, what would it be called?
88. What’s one thing I do that always makes you roll your eyes, but you secretly find it funny? I know I have some goofy habits, though. Lol
89. If we could switch lives for a day, what’s the first thing you’d do as me?
90. What’s the most ridiculous argument we’ve ever had? , I’m sure it was something silly that we can laugh about now.
91. If we had a theme song for our relationship, what would it be?
92. What’s the weirdest food I’ve ever made or eaten that made you question me? I know I’ve had some questionable food moments—can’t lie.
93. What’s your favorite inside joke that only we understand?
94. If I had to do a stand-up comedy routine about us, what would be my opening joke?
95. What’s the most awkward or embarrassing thing we’ve done together?
96. Would you still like it if we became celebrities overnight?
97. What’s the funniest text I’ve ever sent you?
98. If we could prank someone together, who would it be and what would we do?”
99. What’s the silliest nickname I’ve ever called you? I hope you still remember it.
100. If we could relive any funny moment from this year, which one would you pick?
QUICK TIP:
If you want the conversation to feel more fun and natural, you can buy card games and play together.
These card games for couples usually come with 20 to 50 cards, each with a different question. You take turns picking a card at random and asking the question to your partner.
Depending on the theme of the game, the questions can be flirty, icebreakers, or even designed for deeper conversations.
Closing Remarks
Feel free to use any of the conversation starters above.
Ask the questions, enjoy the laughs as the conversation leads you far into discovering different things about your partner, and then move on to the next one.
It’s also a good idea to reflect on the people who have supported you both over the years.
The main point is to keep things natural and take time to appreciate the moment.
