101 Questions to Ask Before Getting Engaged

Getting engaged is a big step, and the best time to talk about the practical side of a shared life is before the ring. This list of 101 questions to ask before getting engaged covers the topics couples most often wish they had discussed earlier: finances and debt, children, where you want to live, careers, families, household roles and how you handle conflict.

You do not need to finish it in one night. Work through ten or fifteen questions per evening, take turns answering and mark the ones you want to revisit. You can read the full list below or press play to get one card at a time on one phone or two. There are no scores - just honest conversation about the future you want to build.

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1
What's one wedding tradition you'd love to keep?
2
What's one wedding tradition you'd happily skip?
3
Where would your dream honeymoon be?
4
What song do you want for our first dance?
5
Who do you think will cry first at the wedding?
6
How did your parents handle conflict, and what would you do differently?
7
Where would you like us to live in five years?
8
How should we divide household chores?
9
How involved do you want our families to be in our life?
10
How do you want to celebrate holidays as a married couple?
11
How do you feel about combining bank accounts?
12
How much time apart do you think is healthy for a married couple?
13
What part of planning the wedding are you most excited about?
14
What do you want our first year of marriage to feel like?
15
What's the vow you most want to keep?
16
How did the proposal feel for you?
17
What's something you want to remember from this engaged season?
18
What's one thing you want to learn from couples you admire?
19
How can we keep wedding stress from affecting us?
20
What's one promise you want to make to me that's not in the vows?
21
How many kids, if any, do you imagine having?
22
How did your parents' approach shape how you'd want to parent?
23
How do you feel about adoption or fostering?
24
How would we split parenting responsibilities?
25
Would you want our kids to grow up near family?
26
How do you feel about pets as part of our family?
27
What's something from your childhood you'd never repeat?
28
How would we keep our relationship strong after having kids?
29
What's your view on discipline?
30
What kind of grandparents do you hope our parents would be?
31
What's a family tradition you'd love to start with our own family?
32
How would you want to celebrate holidays with kids?
33
What role would you want our parents to play in our kids' lives?
34
How do you feel about raising kids in a city versus the countryside?
35
What's a children's book you'd want to read to our kids?
36
How would we share time off after a baby arrives?
37
What would you want our kids to call us?
38
How important is it to you that our kids learn another language?
39
What hobbies would you love to share with our kids?
40
How much screen time feels right for kids to you?
41
What's one thing your parents got right that you'd copy?
42
How would we make sure we still have date nights as parents?
43
What does a successful marriage look like to you?
44
How do you want us to handle money once we're married?
45
What role do you want faith or spirituality to play in our home?
46
How do you feel about having children, and when?
47
What would you do if we fell out of sync for a while?
48
What's a deal-breaker for you in a marriage?
49
What are your expectations around careers and relocating?
50
What do you think we'll argue about most, and how should we handle it?
51
What's one fear about marriage you'd like to talk about?
52
What do you want our marriage to stand for?
53
Do you see children in our future?
54
What values would you most want to pass on to our kids?
55
How would we handle it if we disagreed about having kids?
56
What's something from your childhood you'd want to give our kids?
57
What scares you most about becoming a parent?
58
What does being a good parent mean to you?
59
How would we handle it if becoming parents took longer than we hoped?
60
What kind of family culture do you want us to build?
61
What's a city you'd love to live in someday?
62
What's one adventure you want us to have this year?
63
What's a trip we absolutely have to take together?
64
If we had a family motto, what would it be?
65
Would I rather live in a city or the countryside one day?
66
Do I want to travel the world or settle down?
67
Would I rather have a big house or a small cozy one?
68
Would I rather learn to surf or learn to ski?
69
What country do I most want to visit?
70
Live abroad or Stay close to home?
71
Early retirement or Dream job forever?
72
Farm life or City life?
73
Big wedding or Small wedding?
74
Dog or Cat?
75
House by the sea or Cabin in the woods?
76
Would you rather live in a big city or live in a small town?
77
Would you rather travel the world for a year or buy our dream home?
78
Would you rather have a farm or have a beach house?
79
Would you rather learn a new language together or learn an instrument together?
80
Would you rather have a big wedding or elope?
81
Would you rather adopt a dog or adopt a cat?
82
Would you rather live abroad for a while or never move away?
83
Would you rather build a home from scratch or restore an old house?
84
Where do you see us in five years?
85
What's something you want to achieve before you turn 50?
86
What does your dream home look like?
87
How do you picture our ideal retirement?
88
What's a skill you'd like us to learn together?
89
What's a career change you've thought about?
90
How do you want our weekends to look in ten years?
91
What traditions do you want us to keep forever?
92
What would you like to be doing every day when you're 70?
93
Would I rather retire early or work on something I love forever?
94
Do I want to live near family in the future?
95
Where do I want to live in ten years?
96
What's one thing on my bucket list?
97
What would I do if I didn't have to work?
98
Travel the world or Buy a home?
99
Kids soon or Kids later?
100
Would you rather retire at 50 with less or retire at 65 with more?
101
Would you rather have a career you love or have a job that pays a lot?

What should you know before getting engaged?

You should understand each other's views on money, children, careers, where to live, family involvement and how you resolve disagreements. This list covers all of them.

Do we need to agree on all 101 questions?

No. The goal is to understand each other. Some differences are fine; the important thing is knowing where they are.

How long does it take to go through 101 questions?

Most couples spread it over several evenings, about 15 to 20 questions at a time.

Is this list a substitute for premarital counseling?

No. It is a conversation starter. A counselor or premarital course can help you go deeper if you want guidance.