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Thursday, January 15, 2026

The Love Diaries: The 60 Questions You Should Ask Before Getting More Serious in Your Relationship

Divorce Coach Bridgette Jackson sees plenty of couples who have regrets about what they didn’t do before they got serious about their relationship – so, here’s what to ask your partner before taking the big next step to open communication and make sure you know exactly who you’re committing to!

Welcome to our series, The Love Diaries – a space for you to share your experiences, advice, fairy-tale endings, setbacks and heartbreaks. We’ll be hearing from industry experts giving practical advice alongside Capsule readers (You!) sharing your firsthand experiences with love – from the woman who cheated on her husband with a work colleague, one woman’s temptation now the love of her life is finally single (although she’s not), and the woman who forced her husband to choose between her and his girlfriend. Maybe you haven’t been dating very long, but you’re invested – you want to move in with this person, asap. Or maybe you’ve been dating a long time, living together even and you’ve got marriage on your mind. Or babies on your mind. Or buying a house together on your mind.

It can be such an exciting time taking the next step in your relationship, but, it’s also a good time to do a bit of due diligence and making sure you know exactly what, or rather who, you’re signing up for.

As a divorce coach, Bridgette Jackson from Equal Exes, most often sees couples when they’re in crisis. By the time they come to her, there’s a lot of history and a lot of baggage. But, there’s often also a lot of regret – particularly around communication. “If only we had discussed this!” “If only I knew that about them!” “If only I knew that is how they felt about that!” are things they often say.

So, Bridgette cannot stress enough how important and helpful it is to have open communication and ask some of the harder questions earlier on in your relationship. Then you know what’s on the table – if it’s sometimes not what you want to hear, you have the time and the opportunity to think about whether they’re things you’re able to work with, or whether they’re dealbreakers, before you’re 15 years into a relationship and feel blindsided by these things.

Bridgette also says to trust your gut when it comes to a potential life partner, to get some answers too. “Follow your instinct/intuition rather than your heart,” she says. “If you feel like something is not quite right, believe it. Those red flags waving gently in the wind will become huge banners furiously flashing across your face if you try to ignore them.”

She recommends watching how they treat others before making a big commitment to them. “Watch how the other person treats others – the wait staff at a restaurant, the person who processes the transaction for your meal, and how they treat their ex-partner and their children.”

But, most importantly she recommends asking questions and listening carefully. “We have 60 questions people should ask each other before committing to a serious relationship,” she says. “The questions are not intended to expose incompatibility. Instead, they are about identifying potential differences and working to compromise.”

The 60 Questions You Should Ask

1. Which is most important for you; to be happy or to be successful?
2. How do you think your friends see you?
3. When was the last time you had to apologise? What was it for?
4. How long does it take you to decide and make up your mind on something?
5. What is the best quality you like in people?
6. What about you do people find irritating?
7. What is totally unpardonable for you?
8. A saver or a spender: which best describes you?
9. Would you rather go out with friends or stay indoors?
10. What is the most important value you wouldn’t forsake?
11. What is the most thoughtful thing someone did for you?
12. What is the biggest event you have had to forgive someone for?
13. Would you say religion is important to you?
14. Would you rather be beautiful or brainy?
15. What would you consider a perfect future for you?
16. How open are you to feedback and criticism?
17. How do you cope with people who disagree with you?
18. Have you ever been involved in a physical altercation?
19. What do you do to make me happy that you do not really like?
20. How do you know you are loved and appreciated?
21. What has been the most traumatic event in your life?
22. How did you work through it?
23. What are the biggest lessons that you learnt from it?
24. Do you have any mental health problems?
25. Are there any hereditary illnesses that run in your family?
26. What is your credit report like?
27. Would you take on the responsibility of taking care of your parents when they retire?
28. Are you open to getting married and when do you want this to happen?
29. Are you open to signing a prenup before marriage?
30. In what ways do you expect marriage to change our relationship?
31. Would you rather live in a small or big city?
32. Are you open to relocating to another country?
33. What do you do as a girlfriend/boyfriend that you wouldn’t do as a wife/husband?
34. Do you want to have kids and when?
35. How would you want to raise your kids?
36. How do you feel about adopting a child?
37. What do you regard as infidelity and how would you deal with it?
38. How much do you want to maintain your individuality while cohabiting?
39. Do you like to take control or have someone take control?
40. What do you think we should do to make our relationship better?
41. What is our top priority as a couple?
42. How do you deal with stress?
43. What do you fear most about marriage?
44. Is it better to be loved, admired, or respected?
45. What makes up your bucket list?
46. What do you cherish most about your childhood?
47. When was the last time you cried and why?
48. How willing are you to do your own healing work?
49. What is the most romantic thing you have done for someone?
50. What did you fancy about your first crush?
51. How do you describe me to your friends and family?
52. When and how did you realise you were in love with me?
53. Have you ever experienced heartbreak?
54. What is the best date we have ever had?
55. What easily turns you on?
56. How did you feel the first time we kissed?
57. What is your favourite sexual memory of us so far?
58. What is your secret sexual fantasy?
59. How often do you think we should be having sex?
60. Is there a question that you feel we should have covered and it is not listed? That question is….?

“To sum it all up,” says Bridgette, “the point of asking any of the questions listed above is to listen really carefully and utilise the responses for decision-making regarding the next move to make in a relationship. Also, allow them to elaborate on the answers as much as possible. Just listen.”


Questions reference: Byeliner and Equal Exes

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