31 Questions You Should Ask Your Significant Other

Photographed by Eva K. Salvi.
Talking about money with anyone (even yourself) can be awkward as hell. And it gets even more complicated when you’re having the conversation with the person you’re sleeping with.

I don’t remember my earliest conversations with my husband, Ken, about money. We must have talked about splitting the bill in those early days of dating (just out of college, both totally broke), but I do remember the first time we discussed a big purchase. At the time, he was in a band. I was visiting family in Texas, and Ken called to ask if it was okay if he spent $200 on a bass amp. We’d been talking about moving in together, but hadn’t taken those steps yet. I was thrilled when he consulted me. I took it as a sign that he was serious about the relationship. (For the record, neither of us can remember if he actually bought the amp; the band has long since broken up.)

In the years since, we’ve had hundreds of conversations about money. But even if we don’t always agree, I really like talking with Ken about our finances, because those talks are necessary for planning our future together.

Launching into those conversations can be tough, though. When is it appropriate to have that first conversation about money? Refinery29 financial advisor Priya Malani and I talk about this a lot, and during one chat, she mentioned a client who had a list of 40 questions she asks potential boyfriends. I was immediately intrigued: I had to see that list. And then I wanted to figure out if we could turn this list into something money-focused.

In the end, we trimmed the original list from 40 to 20 questions, and then we added 11 more financially-conscious questions that we think are essentials. Ahead, we walk you through eight major relationship milestones. But here’s the thing: Everyone is different, and some of these questions might not apply to you, you might word them differently, or you might ask them at a different stage. Focus less on the milestones and more on the questions.

The next big issue is when to ask. That’s also a personal matter. I like to talk about money away from home, over drinks or dinner. For other people, drinking and money can be a terrible combination. In the early stages of a relationship, you’ll have some trial-and-error as you try to figure out the ideal time for these (sometimes) difficult conversations.

And don’t feel bad if it makes you feel uncomfortable. Priya and I aren’t saying it’s easy, but we are saying it’s necessary. Yes, it’s scary and awkward, but money powers your future, and there are few things more thrilling than planning a life with someone.

So make a date, and get ready to start talking.
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This is probably not the right time to get into a deep financial discussion. But it is a good time to get to know the basics and be up-front and honest about your expectations.

The questions:
1.What do you do? Do you like your job? Is this something you thought you would do when you were younger?
2. Can I split the bill with you?

Keep in mind:
The issue of who pays the check on the first date is complicated — in fact, it’s so controversial, we did a whole study on the topic. Personally, when I was dating, I preferred to split the bill. I also realize that not everyone agrees with that idea. But I think you’re remiss not to at least offer.

Regarding the job question — it’s a pretty natural first-date topic, and it can reveal a lot about a person’s future plans. If he or she hates work, it might be time to plan a career change or big move in the future. Maybe that works with your future plans; maybe it doesn’t, so isn’t that a good thing to figure out up front?
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You don’t really need to spend those first heady weeks of dating talking about money with your new flame. But around the time you have the “what are we” conversation, it’s good to throw a few money questions in there; now is the time to start really getting to know each other.

The questions:
1. Do you feel like we have an equal relationship?
2. What do you think about marriage?
3. Are you planning any major career changes in the foreseeable future?

Keep in mind:
You might be thinking: We’ve been dating for a month! I’m not going to ask if we have an equal relationship. But why not? Shouldn’t that be taken into consideration if you’re going to see this person exclusively? Think about it. (Also, this is one of the questions on this list that you don’t have to ask word-for-word — but use the idea of the question as a jumping-off point.)

It’s also awkward to talk about marriage, but you’re not asking your S.O. if he or she wants to marry you — just how he or she feels about marriage in general. This can be a good one to bring up if either of you has friends who are getting married; it makes the topic more approachable and less out-of-the-blue.

In the early stages of a relationship, you don’t want to think about a time when you might have to make a life-changing compromise for your significant other — something huge, like quitting your job and moving across the country to support that person's career change. But these things do happen. Wouldn’t it be good to know before you got serious?
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There will come a point when you two decide to make a big purchase together, whether you’re planning a trip (hello, expensive plane tickets), getting a puppy (hello, exorbitant vet bill), or something else entirely. And this is a good time to get into some of the more specific details about money.

The questions:
1. Do you budget? How do you pay bills?
2. What is your savings philosophy?
3. If either of us gets a bonus/wins the lottery, what do I/you/we do with that money?

Keep in mind:
These questions all go hand-in-hand: Your budget is tied to the way you pay bills is tied to the way you save is tied to how you’d spend a windfall. For some people, these are fun questions — they give you a chance to daydream about the future or brag about your clever budgeting skills. For others, budgeting is boring or terrifying or something you don’t think about at all.

Couples need to see eye-to-eye on these topics, but it is good if they’re at least on the same page. I definitely like to spend more money than Ken, but at the end of the day, we have very similar financial philosophies. Spenders and savers can be happy together, as long as you’re open and honest from the start.
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When you decide to take that first big step and move in together, a host of big financial questions will come up. Why not rip the Band-Aid off and get all the awkwardness out of the way before you move?

The questions:
1. How much money do you make?
2. How will we split the rent? How will we split the monthly bills? 50/50 or based on our incomes?
3. Do you have student loan debt? What are you doing about it?
4. Is there anything I should know about your health? Is there anything you are concerned with?
5. Is there anything or anyone in your past I should be aware of?

Keep in mind:
Last summer, Fidelity published a study that found 43% of people don’t know how much money their spouses make. This stat blew my mind. And I know what you’re thinking: We just want to live together; we haven’t reached the marriage phase yet. But once you decide to move in together, you usually have to provide rental agencies or landlords with a ton of personal financial information, including your annual salaries, making this a natural time to discuss how much money you make. And from there, you should have a conversation about how you’re splitting the rent. If one partner makes significantly more, a 50-50 split might not make sense. You need to figure out what works for you.

This is also a good time to touch on a few deeper topics: student loan debt, past relationships, and your health. All of these things can have a major influence on your overall financial picture. Student loan debt is obvious — for many millennials, there’s the feeling that you can’t cross major milestones (like getting married) because of this debt. It’s an awful feeling, but the truth is, the majority of us have some kind of debt, and it’s nothing to feel ashamed of.

Regarding health issues: In the long term, this can be a major expense that might affect your monthly budget and therefore influence how much you spend on rent and other expenses.

And then there’s the most intriguing question on this list: “Is there anything or anyone in your past I should be aware of?” At this stage, you’ve probably (hopefully!) had long conversations about your past, but now is a good time to make sure that there won’t be any unforeseen surprises (an ex-spouse, thousands in credit card debt, a secret double life) in your future. You’re moving in with this person; shouldn’t you know practically everything about him or her?
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You’re going to fight with your S.O. about money. It’s inevitable. And it’s nothing to feel bad about. But after you have that big fight, and things are calmer, it’s important to follow up with a few questions.

The questions:
1. Do you trust me with money? Would you, someday, want a joint bank account?
2. Besides me, whom do you confide in most (or do you confide in someone else more than me)?
3. Who should know about our business (issues, struggles, arguments — obviously we will share the good things)?

Keep in mind:
The question “Do you trust me with money?” is super awkward, and I’m not sure I would advocate you asking it point-blank. But the follow-up, “Would you someday want a joint bank account?” is really important, and in some ways answers the trust question. Whether you decide to merge finances before or after marriage (or never) is entirely up to each individual couple, but you should definitely talk about it, so no weird feelings come up if one of you feels like things aren’t fair.

You might think the questions, “Whom do you confide in most?” and “Who should know about our business?” aren’t about money, but I would argue these are almost as important as the joint bank account question. Is there someone in your S.O.’s life who knows all your business? Is that okay with you? I tell my mom almost everything, but there are things (especially financial matters) that are strictly between me and Ken. At the same time, when we need financial advice, we’ll reach out to both sets of parents (and a handful of other friends and mentors) to get their feedback. It’s good to know whom your S.O. depends on, and how much he or she is sharing — or oversharing (or leaving you out of the conversation altogether).
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There are lots of questions you should ask before getting engaged, because once you do, you’ll have enough on your plate without focusing on some of these bigger issues.

The questions:
1. I do/don’t want you to go into debt to buy an engagement ring. How much do you think we should spend? Where is this money coming from? Would you be upset if we both helped pay for the ring?
2. Is there anything you’d regret not doing or accomplishing if you married me?
3. What are your feelings on a prenup? Does your family have any opinions?
4. Do you want to have children? When?
5. How much should be in our emergency fund?
6. Where do you want to spend our vacation time?
7. Would it be a problem if I went on vacation with my friends without you?

Keep in mind:
Priya and I had a long conversation about the engagement ring question. I know it doesn’t seem romantic to talk about how much an engagement ring costs, but for a lot of couples, this will be one of the biggest single purchases they’ll make, short of a car or house. Why wouldn’t you want to have an honest conversation about how much to spend? Should one partner go into debt so the other can have the ring of his or her dreams? The answer might be yes, which is fine if that’s a decision the two of you make together.

If one partner doesn't have the money to pay for the ring, should the other chip in? Is that something you would be okay with? Yes, these questions are uncomfortable, but I believe they are essential to helping you build a strong financial foundation for your marriage. (And yes, Ken and I had a conversation about ring budget, and I still think his proposal was crazy romantic.)

The prenup question is a little scarier, in my opinion, because who wants to think marriage will end in divorce? But it’s something to consider — especially for couples who get married after they own property or a business, stand to inherit a lot of family money, or are more financially established in one way or another. It’s also important to find out what your S.O.’s family thinks about the topic. Most of the prenup conversations I’ve heard about are fueled by overly concerned parents. (This all goes back to the question of “Who knows our business?”)

While you’re getting all this awkward stuff out of the way, let’s move on to kids. Do you want them? How many? And when? And who will care for these kids? Will one parent stay at home? Or do you imagine a more equal division of labor? All of this can have a big influence on your overall earning potential, so it’s crucial to discuss. One thing to note: Like with so many of these big questions, it’s okay not to be 100% certain on your answer. And you might feel differently next year — that’s totally fine. But even if you’re not clear on what you want in the future, just talking it through can give you some perspective.

The emergency-fund question can be complicated. Yes, you should have an emergency fund — but how much you have in said fund is up for debate. Priya recommends three to six months of expenses. Some people want more than that; others would argue that’s excessive (or an impossible goal — or both). But this is one number you should discuss and settle on, whether you’ve achieved that financial goal or you’re still working toward it.

The vacation question is far less serious, but it’s important to consider in your ongoing conversations about spending. For some couples, you can’t imagine traveling without each other. For others, you need that down time without your S.O. But this is all connected back to decisions you make about spending money together and separately. Maybe your annual Miami beach vacation won’t fit into a budget if you’re saving to buy a house — are you okay giving that up? Talk about it!
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You’ve decided to legally commit yourself to one person for the rest of your life, which means you should be talking a lot about money and your future. Before you even pick a venue, consider asking these questions.

The questions:
1. What are your thoughts on our wedding? Who is going to pay for it?
2. Will an equal relationship mean the same thing now as it does in five years? 10 years, etc.? How do you see us dividing responsibilities over the next five years?
3. If one of our parents or siblings or friends were in need of serious help (possibly to the point of needing to live with us) is that something you’d want?
4. What would we do if we were really, truly unhappy in our relationship?

Keep in mind:
Weddings are expensive, and in 2016, everyone has a different approach for how to pay for them. Is one set of parents paying for everything? Do you want one set of parents to have that much control? Do you really want to shell out tens of thousands of dollars for a single day? Is that money better spent on something else? Before you start planning, these are crucial money questions to discuss with your intended.

But as you’re looking toward the future, you’ll want to touch on topics other than your wedding. It’s a good time to take up that equality question again. If you’ve proposed or said yes, then chances are you’re happy in the relationship. But marriage is a good chance to do a little self-evaluating (why do you think so many churches require couples to go through premarital counseling?). Where do you need to improve and what steps can you take to make things more equal?

You two don’t live in a bubble, though, and throughout your relationship, outside factors, including your family and friends, will influence the stability and happiness of your marriage. Maybe you’ve already dealt with these kinds of problems. But as you’re looking to combine your financial lives, it’s good to discuss issues like your extended family (and friends) and money. In a hypothetical situation, how would you react if a family member needed money or a place to stay? Your reaction might be different once the situation becomes a reality, but at least you’ll have a sense of how you might handle the problem.

The last question is another big one, and like the “Do you trust me with money?” question, it’s not an easy one to ask outright. But relationships take work, and when you’re married, breaking up is more complicated, because there is a legal contract involved. So if (when) you hit bumps in the road, how are you going to deal? Do you believe in couples’ therapy? Do you believe in divorce? Talking about these big questions in a hypothetical sense won’t guarantee you never have to deal with the problem in real life, but it can help prepare you if (when) they do come up down over the course of your relationship.
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Personal finances are complicated when there are just two people involved. Throw a baby into the picture and everything changes. Money and kids are inextricably linked, and it’s best to have these tough conversations before you start popping them out.

The questions:
1. How do you want to raise our children? How would we take care of our children? Who would watch them?
2. What would we do if one of us got sick? Do you have life insurance?
3. How would we handle a career break?
4. How close would you someday like to live to your parents? To my parents? Do you have a plan to care for your parents? Have you ever discussed this with your siblings?

Keep in mind:
I think these are some of the hardest questions to discuss, because even if you’re on the same page about having kids, you might not see eye to eye on how to raise them. And kids are expensive. In New York, it’s something like $500,000 per child, and elsewhere in the U.S., it’s around $245k. And that doesn’t even begin to touch on the emotional and professional toll.

Sure, your plans will probably change once the baby is no longer a hypothetical, but if you start these discussions early, you can start saving and properly preparing for the way it will upend your daily life. Along with the questions about how you want to raise your kids, you also need to discuss how you’ll care for them, and whether you have life insurance in case something bad happens.

It’s also important to talk about employment breaks. Whether that’s deciding to take time off to raise kids, handling layoffs, or planning for a career change, there’s a good chance that you and your S.O. will face at least a period of unemployment over the course of your relationship. Talking about it (and having a healthy emergency fund) is a good way to prevent some of the stress you feel when these unexpected changes occur.

Down the line, you’ll also want to talk about your parents and any plans to care for them in their old age. It is one of the most depressing conversations you can have, but try to approach it purely from a practical standpoint. Are you planning on living near them as they get older? Do you need to save money to help with their care? And do you have siblings who might shoulder the burden (whether that’s financially or emotionally)? No, these conversations aren’t as joyful as the ones about raising a family, but that shouldn’t stop you from having them.
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