14 Relationship Questions to Ask Before Getting Serious

So, you’ve been dating a guy you like. A lot. Now you’re wondering how serious you should get with him. Or maybe you’ve been serious for a while and are wondering if you should move on to marriage.

I’ve put together some reality-check relationship questions to ask before getting serious that can help you avoid upset and heartbreak down the road. You’ll dive deep into what really makes him tick, and I’ll give you tips for how to interpret his answers.

The more deep relationship questions you ask your boyfriend before getting serious, the better chance you’ll have to know how compatible you are on the big stuff.

We can all get used to someone’s quirks, but we can’t always live with their deeply ingrained philosophies. And the only way to know what those are is to ask the deep relationship questions before you commit.

black man and white woman in relationship talking near window

1. What Do You Consider Cheating?

Yep, I started with one of the big guns. If you really want to know how committed your boyfriend is in a relationship, asking this relationship question will give you a major clue.

The guy who answers “having sex with another woman” is not the guy for you, if you’re wanting a serious relationship. There is a lot of territory between flirting with another woman and sleeping with her that can be considered cheating.

This relationship question requires you to decide what you consider cheating to include. These ideas may or may not be cheating, but perhaps they make you uncomfortable, which should be reason enough to discuss them.

  • giving non-sexy compliments to another woman (You have great taste in music.)
  • sexy flirting (Wow, you’ve got the best butt in this bar.)
  • kissing on the cheek or kissing on the lips
  • holding hands
  • giving massages
  • buying a gift for a woman who is not related to him
  • late night texting or DMs
  • hiding phone conversations and texts
  • eating alone with another woman outside of a work lunch

Take some time to talk about what you both consider to be acceptable in your relationship so you know where the boundaries are that work best for you both.

2. What Is Something You’ll Never Compromise in a Relationship?

This relationship question can bring up some interesting answers.

If a guy answers with, “I will never give up my freedom and independence to do the things I want to do,” then you’ll want to carefully figure out exactly what that means.

If he’s spending 20 hours a week with his buddies to rock climb, mountain bike, or play video games, that’s a red flag. But if he’s only putting in 5 hours a week on cycling or rebuilding a classic Corvette, then it’s not too big of a deal.

You both should have activities that you do separately anyway. The key is to not allow one person’s hobbies and interests to outweigh the needs of the relationship to spend time building your connection.

3. Do You Think Secrets Are Okay in a Relationship?

As far as serious relationship questions goes, this is one that you might not have thought to ask. You’re probably assuming the answer is just “no.” The key to this question is about reading their body language to see if they’re hiding the truth when they answer this relationship question.

No, secrets in a relationship are inherently not good, when you consider that most secrets mean you’re being dishonest or deceitful.

Secrets that hide surprises in a relationship can be ok, such as when he’s saving up to buy tickets to your favorite band’s concert.

See what he responds with when you ask the general question, then dig deeper about these:

  • white lies and what you think are white lies
  • hidden bank accounts
  • hiding purchases
  • keeping feelings/worries hidden
  • not disclosing medical or financial information

Before getting serious, see what he thinks about hiding things or information in general. Ask if past relationships had hidden secrets. It’ll be helpful for understanding how honest your boyfriend is and how he feels about secrets.

4. What Is a Life-Changing Lesson You Learned from a Past Relationship?

Now you get to see if your boyfriend is open to improving and becoming a better person, or if he always stays stuck in his old ways. This is a great question to ask before taking the next step because you need to know if he’s evolving and maturing into a responsible adult.

If he says something flippant like “not to trust blondes,” give him your best unimpressed look and ask him again. Don’t let him off the hook until he provides an answer to your question that’s better than a lame attempt to change the conversation.

Hopefully his answer to this relationship question will be something like “that I should be more aware of her happiness and needs too”  or “not to waste time on a person who doesn’t share my values.”

These responses show he learned lessons about selfishness and the value of time. His self-awareness will tell you that he’ll be more careful about these kinds of priorities when he’s in a relationship with you.

man in blue plaid shirt holding head in hands

5. What Do You Think About Expressing Your Feelings?

If you’re in touch with your emotions (you’re a Cancer, Pisces, INFJ, etc.), one of the best relationship questions to ask is this one.

We’re the ones who swooned over Aragorn crying or emotionally hugging his fellow adventurers in Lord of the Rings. So if that’s you, then you’ll need a partner who is willing to be open to expressing all of his feelings, not just the angry ones.

Ideally, your boyfriend will respond to this relationship question without making fun of his friends or past women in his lives. You want a response that shows that even if he may not be all that expressive, he can accept it in you and show a little of his own. Maybe he didn’t cry at the end of Avengers: Endgame (REALLY?), but he felt super sad and talked about it.

It’s ok if your emotional expression level isn’t the same as his, but you need to know if he can meet you in the middle to ensure your needs are met.

6. Why Are You Still Single?

Here’s a fun one! This question gets a bad rap because no one likes to be called out on being single when they’re well aware that they’re single. But hear me out. I’ve written the tricks to understand his response so you can decide if you want to move forward.

  • “Uhhhh…ha…um, same reason you are??”
    • A deflection technique showing he has not done much contemplation about what he brings to a relationship to make it successful (or how he’s always tanking the relationship).
  • “Guess I’m bad at picking women.”
    • A self-deprecating answer that gives you a perfect chance to ask what kind of women he usually dates. If he lists a bunch of train-wreck qualities, run. Clearly he has some issues that keep bringing the wrong kind of women into his life. What does that say about what he thinks of you?
  • “They all want more commitment than I’m willing to give.”
    • This answer is clear. He’s a commitment-phobe. Run far away if you’re looking for something long-term and committed.
  • “I always bring home women that my mom (or sister/friend) ends up hating.”
    • Ooooh, this one is tricky. Is he bringing home awful women or is his mom a high-standard and too-involved mommy for this mama’s boy? Use these follow-up questions: “What didn’t she like? How soon is she meeting your girlfriends? Has she ever approved of anyone?” If it’s a mom problem, the right woman will help him stand up to her and make the relationship last. You’ll have to decide if that’s you.
  • “I guess I’m just really happy with where my life is at, and it’s going to take someone amazing to join me.”
    • This is the ideal answer. It shows he’s confident with the life he has created, and that it’s probably well balanced. He’s looking for someone who can meet him on his level, and you’re potentially on that list.

7. What Do You Spend the Most Money On?

Now you get an insight into his financial habits, which is critical for relationship success. Don’t skip asking this question before getting married or moving in together!

The list could be endless: designer shoes, video games, travel, eating out, investments, student debt, watches, books, etc.

If his answer is student debt, that can be ok because it shows he’s trying to be financially responsible. Just know that you may have to carry some of the financial load for extra expenditures for a while if you get serious.

If he spends on designer shoes, does he have a limit of how many he buys? Is he going into debt?

The key here is to identify if the spending habits are unhealthy and out of control or within reason. Money matters are a top reason couples don’t get along, so use this lighthearted question to understand his spending habits early on.

8. What Are Your Top Deal Breakers?

I think this is one of the most overlooked relationship questions.

We probably assume the other person’s deal breakers are the usual: cheating, lying, gambling, smoking, etc. But there are a lot more things that can be a deal breaker for people, and you have to ask to find out.

When you ask your boyfriend this question, he might say, “I can’t stay with someone who doesn’t respect or listen to my opinions.” This answer can tell you a lot.

He’s probably had a past relationship where his opinion was disrespected constantly, or he grew up in a house where his parents never cared about the other person’s opinion. This can be your chance to shine by showing him how you believe his opinion matters because you are a healthy communicator.

Other top deal breakers could include being consistently unreliable, not wanting kids, different money management styles, health habits, political/religious views, not communicating enough, or never helping to pay for dates/food/activities, etc.

9. Do You Want Kids and What Is Your Parenting Style?

Yes, this is also a deal breaker topic, but it’s a big one so we’ll discuss it separately. If you want kids, then you absolutely have to ask about this so you find out if you’re on the same page.

Let me be clear about one thing: you cannot expect a man to change his opinion about having kids after you get married if you want them and he doesn’t.

That is a major error many women make with the man they think is perfect for them, except he’s not into having kids (yet). “Yet” is what they tell their girlfriends, while he’s telling his buddies that his awesome woman won’t ask to have kids again because he made that clear before they got married.

Few men actually change their mind and want to have kids, but you can’t expect it. You’d be setting the relationship up for failure with mismatched expectations.

If he is open to kids, you need to know how he plans to parent those kids. Is he authoritarian? Is he hands-off and never wants to be involved? Will he let them be kids and never say “no”? Does he want to be involved every step?

Get clear about your expectations to make sure they align. Parenting is yet another one of the top reasons for dissatisfaction in a marriage. Choose to ask this relationship question first and avoid conflict later.

10. What Will You Bring to Our Relationship?

When you ask this question, definitely be prepared to answer for yourself too. He’ll be curious after he’s been put on the spot. It’s a fantastic question to ask before getting serious because you don’t want to be the only one putting in effort.

Again, watch out for flippant answers like, “I’ll bring home the bacon, and you can cook it.” Oh gosh, I hope his answer isn’t that misogynistic. You get the point though. He’s clearly saying he’ll make money and that’s enough.

No, honey, it’s not enough. You’ve got your own job that keeps you busy, so you need someone who understands that healthy relationship participation involves more than just earning money.

Smarty-pants answers filled with sarcasm usually hold some level of truth to them, so be on the lookout for them.

Hopefully, he’ll answer with something that shows he’ll help pitch in with household duties, cook meals, spend time with your family/friends, bring emotional support/stability, loyalty, etc.

man and woman cooking in kitchen together asking relationship questions

11. Do You Believe There Are Specific Roles in a Relationship?

This relationship question is helpful for exposing underlying beliefs that may not surface as quickly.

Some guys can fake a few beliefs about women’s roles for a while, but you’ll want to read his body language when he answers this relationship question to know the truth. If he squirms or looks away quickly when he says, “no,” make a mental note.

Ideally, there should only be one area that has a specific role: pregnancy, for obvious scientific reasons. Aside from that, your boyfriend should definitely be open to helping around the house. Maybe he prefers some tasks more than others, such as taking out the trash over dusting the shelves. That’s not an issue as long as he kindly raises his distaste for it, and you’re ok with doing the dusting.

He may actually want to take on the role of the “more manly” duties such as mowing the lawn or fixing the leaky faucet. The problem comes if you really enjoy doing those things, and he makes it clear that you shouldn’t be doing them since he’s around. That’s a problem with gender roles.

My best friend has a great husband who happily admits that most of their power tools are hers—and it works great for them!

If he answers that there shouldn’t really be roles, but that, really…there are, press him to see what he means. Then you’ll get to the truth. If he says he thinks women enjoy some things more than men, ask which things. Women aren’t made to do any household task any better than any man. Period.

12. What Did You Like/Dislike About Your Parents’ Relationship?

If you want to understand how your boyfriend was influenced by his childhood, this is a must-ask question before you go too far down the commitment road.

Our families are where we learned to socialize and create feelings of intimacy or closeness. Some families, unfortunately, did not teach healthy lessons at all, and others were the best possible learning grounds for healthy relationships.

Your boyfriend may answer this deep relationship question by sharing a piece of his painful past, and how it influenced him to become a better partner in a healthy relationship. If so, be kind and understanding and try to acknowledge how you’ve seen him show that improvement.

Understanding how his parents’ relationship affected him will give you insights about the kind of partner he will be. He’ll share important values with you that you can build on together.

13. What If Your Friends or Family Don’t Support Our Relationship?

Ooh, a tough one that might not have a great answer unless you’ve been dating for a while.

Obviously, the answer you want to hear is that he’ll stand by you no matter what. What you need to hear is whether or not he knows that. Why? Because some men are extremely attached to their mom/dad/sister/friend’s opinion of who they date. And no woman may ever live up to that expectation.

The right guy should understand that his family has an opinion, but if the two of you are a great couple who help each other be their best self and want to be together, then your relationship is what comes first.

If it’s a friend who can’t accept the relationship, then your boyfriend should take time to have them explain their concerns. It could be rooted in jealousy, concern about your past, fear of change, or even a need to control the friendship. The right guy will know how to move forward (or not) with that friend, if he’s chosen to make you a priority.

14. What Do You Want Out of This Relationship?

Ok, this question to ask before getting serious is another one that is often overlooked. It seems too basic because we often assume that the answer is the same as ours. But what if it’s not?

Excluding hook-up dates, since you’re reading this because you want a healthy and successful relationship, there are still a few different reasons why a person would want to get into a relationship.

  • loneliness
  • someone to share costs in an expensive city (yep, it’s true)
  • looking for marriage
  • wanting to start a family (ticking clock)
  • permanent best friend with benefits

Admittedly, most singles want a relationship because we’re lonely on some level. That’s not inherently bad. What’s bad is when you’re not ok with being “sad and alone,” so you’re desperate for a relationship. Relationships are not a guarantee of happiness. You are the creator of your own happiness.

If your boyfriend answers that he’s tired of being alone all the time, it can be a red flag because it shows that he’s not necessarily looking to contribute and grow in a relationship. You want someone who will be your partner, not your leech. 

The ticking clock answer is also a bit of a red flag. Rushing into a committed relationship with marriage as the end goal is not the solution to feeling like you’re getting too old to start a family much later than…now. Marriage isn’t a sprint, it’s a marathon.

Armed with these 14 relationship questions to ask before getting serious with your boyfriend, you’re ready to see if he’s ready to commit to something more. And you’re prepped and ready to interpret his answers so you know exactly what he’s thinking. 

The sooner you find out your boyfriend’s answers, the sooner you’ll know if he’s the right guy for you or if it’s time to move on.

Which of these questions are you most excited to ask your boyfriend? Share in the comments below!

white man and woman in formal clothes talking on tin can telephone 


  1. Michal May 30, 2020
    • Brie May 30, 2020
  2. Dev May 30, 2020
    • Brie May 30, 2020

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