40 Questions to Ask Before Getting Engaged (Without Making It Weird)

2 November 2026

Getting engaged is a big step, and it’s easier when you already know how you each think about the everyday stuff: money, family, home, kids, and how you handle a bad week. These 40 questions to ask before getting engaged are grouped from easy to more serious, so you can warm up and then get to the real conversations. They’re not a test and there are no right answers. Take turns, answer your own question too, and either of you can pass or come back to a question another day.

TL;DR

• Start with the easy “what’s daily life like” questions, then move towards money, family and the future.
• You’re not looking for identical answers, just for understanding and room to work things out together.
• Take turns asking, and answer your own question as well.
• Either of you can pass, no reason needed. “Let’s come back to that” is a perfectly good answer.
• Spread them over a few evenings rather than one big sit-down.

Easy warm-ups: how we live day to day

Marriage or not, you’re mostly signing up for ordinary days. These are a friendly way in.

1. What does a perfect ordinary weeknight look like for you?
2. How do you like to split up household jobs, and which ones do you secretly hate?
3. Are you a “plan the weekend in advance” person or a “see how we feel” person?
4. How much alone time do you need to feel like yourself?
5. What’s a habit of mine that you’ve come to love, and one you’re still adjusting to?
6. How do you like to be looked after when you’re sick?
7. What’s one small thing I do that makes your day better?
8. What does “home” mean to you?

Money: the practical bit

Money is a topic many couples put off. Start gently and keep it curious rather than accusing.

9. What was money like in your family growing up, and how has that shaped you?
10. Are you more of a saver or a spender, and how do you feel about that?
11. How would you like us to handle money together: joint, separate, or a mix?
12. Is there any debt or financial worry you’d like me to know about when you’re ready to share it?
13. What’s something worth spending on, even when money’s tight?
14. How do we want to make bigger decisions, like a major purchase?
15. What does feeling financially secure look like to you?

Family and friends

You’re not just joining your lives, you’re joining two sets of people. These help you talk about it kindly.

16. What’s your family like at their best, and what’s a tricky bit I should know about?
17. How often would you like to see family, and how do you picture holidays working?
18. Which traditions from your family do you want to keep, and which would you happily let go?
19. How do you feel about my family and friends? Is there anything you’d like to feel easier?
20. How would we like to handle disagreements with relatives so we stay on the same team?
21. How much time do you want with friends on your own?

Kids, work and where we live

These can be big ones, so go slowly. Honest and unfinished is better than neat and rehearsed.

22. How do you feel about having kids, and what are you picturing?
23. If kids are on the table, how would we want to share the work of raising them?
24. What matters most to you in your work or career right now?
25. If one of us had a chance to move for work, how would we make that decision?
26. Where would you love to live one day, and what’s most important about the place?
27. What would a good balance between work and time together look like?
28. Is there a dream or goal you haven’t told me much about?

Handling the hard moments

Every couple gets stressed or disagrees. Knowing how each of you works is a real head start.

29. What do you need from me when you’re stressed or upset?
30. What’s the best way to bring up something that’s bothering me?
31. How do you like to make up after an argument?
32. What’s a conversation we’ve found hard, and what helped?
33. When have you felt most supported by me?
34. Is there something you’ve found hard to ask for?

The wedding and the bigger picture

Plenty of people spend more time planning the day than the life after it. These keep both in view.

35. What does being engaged mean to you, and what are you hoping changes?
36. What would your ideal wedding feel like: big, small, or something different entirely?
37. How would you feel about the planning, and who might do what?
38. What does a good marriage look like to you? Who’s an example you admire?
39. What are you most looking forward to about our future?
40. Is there anything you’d like to talk about that we haven’t yet?

How to use these questions

Don’t do them all at once. Pick three or four and spread them across the week. A walk, a long drive or a slow dinner usually works better than a formal sit-down.

Take turns. If you ask a question, answer it too. It keeps things fair and a bit lighter.

Listen first. When your partner answers, try summing it up before you respond. You don’t need to fix or argue anything on the spot.

Pass freely. Either of you can skip a question, no reason given. If something feels heavy, park it and come back another time.

Different isn’t a red flag. Most couples don’t answer everything the same way. What matters is whether you can talk about it kindly and find a way forward.

Know when to get help. If a conversation keeps getting stuck, a counsellor or relationship professional can be a good support. There’s no shame in it.

FAQ

What are good questions to ask before getting engaged?

Good questions cover everyday life, money, family, kids, where you want to live and how you handle conflict. The list above starts with easy ones and moves to more serious topics, so you can build up to them.

How long should we be together before talking about this?

There’s no set timeline. Many couples talk about these topics as their relationship becomes more serious, long before any ring. What matters is that you’re both comfortable having the conversation.

What if we disagree on something big?

Disagreeing doesn’t mean the relationship won’t work, but it’s worth taking seriously. Listen to each other, get curious about the reasons, and take your time. If it’s something you both find hard to resolve, talking to a counsellor can help.

Can we use these if we’re not planning to marry?

Yes. They’re just as useful for moving in together, committing to a long-term future, or simply knowing each other better.

Prefer to draw your questions together?

If you’d like something to do the choosing for you, Candid is a private connection game for couples. You draw prompts together from one deck on one phone, across four categories: Icebreaker, Deep Truths, Flirty Dares and Intimate. You take turns drawing, either of you can pass anytime, and there’s no scoreboard. There’s also a Desires match, where you each pick privately and only the choices you both made are shown. Nothing leaves your phone. Candid is on iPhone (iOS 18 and later).