25 Questions to Ask Before Getting Serious in a Relationship

If you’re Googling “questions to ask before getting serious in a relationship,” I already know where your head is at. 

You’re not in panic mode. You’re not looking for red flags to run from. You’re in that in-between stage where things feel good, maybe really good, and you’re smart enough to know that good feelings alone don’t build a life together.

I’ve been there… Before my husband and I got engaged, I made him sit through what he still jokingly calls “the interview,” a long weekend where I brought up money, kids, in-laws, and what would happen if one of us got a job offer across the country. 

He thought I was being intense. Looking back, six years into marriage, it’s one of the best things we ever did for us.

I’m not a therapist and I don’t have a degree in relationship psychology. What I do have is a marriage that’s held up through many trials, and enough small arguments about dishes to fill a book. 

I’ve also spent years talking to friends about their relationships, watching which ones lasted and which ones quietly fell apart once the honeymoon phase wore off. The pattern I noticed almost every time? The couples who made it had actually talked about the hard stuff before it became urgent.

So here are the 25 questions I think matter most, organized into categories so you can work through them at your own pace. 

You don’t need to ask all 25 in one sitting (please don’t, that’s a lot even for me). Spread them out over weeks or months. Let them come up naturally over dinner, on a drive, or during a lazy Sunday morning.

Why These Questions Matter More Than “The Talk”

Most relationship advice focuses on one big DTR (define the relationship) conversation. 

In my experience, that’s the wrong approach. One conversation can’t cover everything, and putting all the pressure on a single talk makes both people defensive. 

Instead, I think of these questions as an ongoing audit, little check-ins that build a real picture of whether you’re compatible for the long haul, not just for right now.

Values and Life Goals

These are the foundational questions. Get these wrong and everything else gets harder.

1. What does a “successful life” look like to you? 

Not career success specifically, but life overall. I asked my husband this on our third date and his answer (something about having time for people over having a big title) told me more than a year of small talk would have.

2. Do you want kids, and if so, how many? 

My husband and I were child-free from the very start, we were on the same page about it from our earliest conversations, and that’s stayed true ever since. 

I know that’s not the norm, and I count us lucky that it never needed to be negotiated.

But I’ve watched too many friends assume they were aligned on kids without ever actually saying the words out loud, and find out two years in that they weren’t, sometimes after a wedding, sometimes after a lease was signed together. 

Even if it feels obvious, or you’re sure you already know the answer, ask it directly. Ask it more than once, because people’s answers can genuinely evolve over the course of a relationship.

3. What role does religion or spirituality play in your life, now and in the future? 

Even if neither of you is religious now, this can shift, especially once kids are involved. I’ve seen this become a bigger issue than money in some marriages I know.

4. How do you define loyalty and commitment? 

People have wildly different definitions here, especially around things like opposite-sex friendships, social media behavior, and what counts as “cheating.”

5. What matters more to you: stability or adventure? 

Neither answer is wrong, but a mismatch here (one person craving routine, the other craving spontaneity) causes real friction if you don’t talk about it early.

Money and Practical Life

I used to think talking about money early was unromantic. Now I think it’s one of the most caring things you can do for a relationship.

6. How do you feel about debt? 

Student loans, credit cards, how you were raised to think about borrowing. This shapes so much of how a couple manages money together.

7. Are you a saver or a spender? 

My husband and I are opposites here. But knowing this about each other early allowed us to build systems (like separate “fun money” accounts) instead of resenting each other over every purchase.

8. How do you picture combining finances, if at all? 

Fully joint, mostly separate, a hybrid. There’s no universally right answer, but you need to actually agree, not assume.

9. What does financial security mean to you? 

For some people it’s a specific number in savings. For others it’s just “no debt.” 

Knowing your partner’s number (literally or figuratively) helps you plan together instead of past each other.

10. How was money handled in your family growing up? 

This shapes people more than they realize. I’ve seen families fight about money constantly, which is part of why financial transparency became a non-negotiable for me.

Family, Friends, and Support Systems

11. How involved do you want extended family to be in our life? 

Holidays, weekly calls, living nearby. Get specific, because “family is important to me” can mean very different things.

12. How do you handle conflict with your parents or siblings? 

This tells you a lot about how they’ll eventually handle conflict with you.

13. What’s your relationship like with your ex(es)? 

Not to snoop, but to understand what healthy boundaries look like to them in practice.

14. Who are your closest friends, and what role do they play in your life? 

A partner who has no close friendships outside the relationship can be a red flag. So can one who prioritizes friends over you in ways that feel unbalanced.

15. How do you want to handle it if our families don’t get along? 

Many people don’t ask this one before marriage and end up regretting it later. Navigating two very different families can be difficult, and having a plan earlier can save you some rocky holidays.

Communication and Conflict

16. How do you prefer to resolve arguments? 

Do they need space and time to think, or do they want to talk it out immediately? Mismatched conflict styles cause more damage than the actual disagreements do.

17. What did conflict look like in your household growing up? 

This is one of the most underrated questions on this whole list. People often repeat (or overcorrect from) what they saw modeled at home.

18. How do you feel about couples therapy or counseling? 

I bring this up early with anyone I coach through relationship questions on the blog. A partner who’s open to counseling as a tool, not a last resort, is showing you something important about how they handle hard seasons.

19. What makes you feel most loved and appreciated? 

This is basically a softer version of the love languages idea, and honestly, I think it’s more useful than the quiz itself. Ask it plainly and listen to the actual answer.

20. How do you feel about jealousy, and what triggers it for you? 

Everyone has some capacity for jealousy. Knowing what sets it off and how they typically respond to it helps you avoid unnecessary landmines.

The Future You’re Building Together

21. Where do you see yourself living in 10 years? 

City, suburbs, another country entirely. If one of you is dreaming of a farmhouse and the other can’t imagine leaving downtown, that’s worth surfacing now.

22. How do you feel about relocating for a career opportunity, mine or yours? 

This one is deeply personal to me. My husband had to move for my job, and I’ve had to also do the same too.. and it only worked because we’d talked through the “what if” scenario long before it became real.

23. What are your non-negotiables in a partner? 

Not preferences, actual non-negotiables. Everyone should have a short list. If theirs and yours are incompatible, better to know now.

24. How do you want to divide household and mental labor? 

Chores, planning, remembering birthdays, managing the calendar. This sounds unromantic, but unequal mental load is one of the top things I hear about from readers whose relationships are struggling.

25. What does a good partnership look like to you, day to day? 

Not the wedding, not the proposal, just an ordinary Tuesday. 

This question tends to surface what people actually value versus what they think they’re supposed to say.

How to Actually Ask These Without Ruining Date Night

A few things I’ve learned from personal experience and writing about relationships on this blog:

• Spread them out. Pick one or two per week, not a rapid-fire interview. Nobody wants to feel like they’re being deposed.
• Ask, then actually listen. The point isn’t to check a box, it’s to understand the person you’re building a life with.
• Revisit answers over time. People change. What felt true at 25 might not feel true at 32. I’ve had answers to some of these questions shift for me and my husband over the years, and that’s normal.
• Notice how they respond, not just what they say. Defensiveness, deflection, or refusal to engage with a question honestly tells you something too.
• Be willing to answer them yourself, first if needed. Vulnerability tends to invite vulnerability.

A Few Honest Thoughts Before You Go

I want to be clear about something: there’s no perfect score here. You’re not going to find someone who matches you on all 25 points, and you shouldn’t expect to. 

What you’re really looking for is alignment on the big things and a shared willingness to work through the smaller mismatches together.

When my husband and I did our version of this years ago, we didn’t agree on everything. 

But we agreed on how we wanted to handle disagreement, and that’s turned out to matter more than agreeing on the disagreements themselves.

If you take one thing from this post, let it be this: asking these questions isn’t unromantic, and it isn’t a sign that something is wrong. 

In my experience, it’s one of the clearest signs that something is right. The couples I know who did this work early are, almost without exception, the ones who are still going strong.

Frequently Asked Questions

When is the right time to ask these questions? There’s no single right moment, but most of these are worth bringing up before you move in together, get engaged, or make other major joint decisions. Some, like values and family involvement, are worth raising even earlier.

What if we disagree on some of these? Disagreement isn’t automatically a dealbreaker. What matters more is whether you can talk about the disagreement openly and find a way forward together.

Should we ask these all at once? I wouldn’t recommend it. Let them come up naturally over weeks or months so the conversations feel real instead of like an interrogation.

If this resonated with you, I’d love to hear which question stood out most, or if there’s one you’d add to the list. Drop it in the comments, I read every single one.