30 Deep Questions To Ask Someone Before You Get In Too Far

Stopping yourself from falling for the wrong person is easier than mending a broken heart. These deep questions will tell you who they really are.

There is nothing more spectacular than falling in love. The problem is, while we are falling in love, there are often red flags that we ignore. Wanting a relationship to work, we neglect those things that are sure to be a deal breaker for a happily ever after.

Before you fall too deeply in love, it is important to know some things about your mate. They may not seem like a big deal during the honeymoon phase, but they could be the cause of your relationship’s demise later on. Asking someone these deep questions early on can save you from big heartache later.

30 deep questions to ask someone you want to date

These questions will provide you with serious, thoughtful insight into your partner’s innerworkings, and will go a long way in determining if you are made for each other… or doomed to fail.

#1 How many children do you want? The question of children is a critical one that most people don’t discuss early enough. Thinking they may scare their mate off, or are being pushy, they don’t ask this question, but it often ends up being a dealbreaker down the road. There may not be that great a difference between one and two, but there is between six and none!

#2 Do you think stereotyping is a good thing? Some people see stereotypes as a useful tool to navigate the world, while others believe they are limiting. People who are okay with stereotypes are fundamentally different from those who think they are bad. Knowing where you stand on the spectrum, as opposed to the person you are with, is imperative for harmony in the future.

#3 Do you have any prejudices? If someone is very prejudiced, it can alter the way you look at them. We often keep our harder beliefs hidden until later in the relationship. Putting it all out there is important, because you want to know how someone feels up front, so it isn’t a surprise or a deal breaker once you have fallen in love.

#4 Do you think men and women are equal? If you are someone who believes a girl can do anything a guy can do, while she is more of a “guys are protectors and women should stay at home” kind of gal, there are going to be problems in the future. Having similar ideas about gender responsibilities and limitations are important to determine roles as you become a couple.

#5 Where is a woman’s place? You want to stay home, but he wants you to work. See how that can cause a problem? If you are a working girl now but want to stay at home with the kids, that is important to discuss before you are knee-deep in a mortgage and a growing family.

#6 Which is more important: family or money? Does she believe in sacrificing family time to be more financially secure, or does she think that money can’t buy happiness? What are you both willing to do without—time or money? Worker bees and leisure-seeking individuals often do not meld well.

#7 What type of relationship did you have with your parents? Did they get along with their parents? The apple usually does not fall far from the tree. Finding out if he got along with his parents will tell you what type of family life he had, and whether it was open and loving or critical and challenging. That is important, because history has a tendency to repeat itself. If his parents were harsh and overly critical, it is more likely that he will unconsciously follow suit when he has children.

#8 If you could go anywhere, where would it be? Is he an adventurer or a history buff? If you like to climb mountains and he would rather grab a good book on the beach, that could cause problems in your future. It isn’t that opposites don’t attract, but if you have nothing in common but being fun to look at, it will make for a challenging union.

#9 Is an expensive car necessary to you? This question will tell you what they value. An expensive car is usually something people get to show off to others. If you are someone who drives a late-model Monte Carlo not because you have to, but because you don’t care, then you probably don’t value appearances as much as he does. Having different mindsets about the importance of what you show to the world can cause real difficulties about spending habits.

#10 If I loved something, would you support me—no matter what? What if you wanted to go on a sabbatical to Africa to help underprivileged children? Would they be willing to let you go, and support you in your dreams? Likewise, if you wanted to become a porn star, would they be okay with it and back you up? It is important to know where they stand on fostering your dreams and if they will provide you with unconditional love and support.

#11 If your parents didn’t like me, would you stick up for me? In-laws can be a very positive or destructive force in a relationship. They may like you now, but if something happened to change the dynamics, who would your spouse back? To be a couple, you have to promise to have your spouse’s back, even when it means standing up to your parents.

#12 Do you often feel lonely? If someone is lonely, they are more likely to want a closer relationship where you do everything together. If you are more of an independent soul, that could leave one person always feeling isolated and sad. That will eventually lead to problems.

#13 If I asked you to do something you weren’t comfortable with, would you do it? There are times in a relationship when someone may want or need something from you that may be uncomfortable for you. Ideally, you want someone who is willing to stand up for themselves and what they want, but you have to know to what extent. If they always put you first, it can lead to losing respect for them. If they always put themselves first, it can make you feel less loved. It is important to know where they stand on this issue and what their beliefs are with regard to what you should do for your partner in a relationship.

#14 Who is more important—you or the person you love? Do they put the person they love before themselves, or do they believe their needs go first? The way that they answer may give you a clue about what is truly inside.

#15 Do you care how many people I have slept with? Are they a jealous person? Every time you see an old love, are they going to make an issue of it, or use it to belittle you, or make you feel poorly? If they don’t care, maybe you want them to a little. Figure out which end of the spectrum they fall on.

#16 What is the worst thing anyone can say to or about you? What is it that defines a bad person for them? If they think the worst thing anyone can think of them is that they are selfish, you are likely to have found someone who puts others first. If they don’t want someone to think they are poor, you probably have someone who is worried about appearances. Who do they want to be?

#17 Are children better seen and not heard? How do they view children? Do they want to parent as a team, or is it couple first, children second? Neither is right, but it is important to know how they view children in a relationship and what place kids will hold.

#18 What behavior is a deal breaker? Do they believe that behavior like bullying or crying are deal breakers? If smoking is a no-no, you should know that before you admit that you smoke when you drink. You can’t hide it forever, nor do you want to, whatever the behavior is.

#19 How many times a week do you think married people should have sex? What are their expectations about what a healthy sexual relationship is? Most people think sex should happen all the time in the beginning. Then, when children come along, romance and sex take a backseat. It is important to know how much they value sex in a relationship over the long term.

#20 How adventurous are you in the bedroom? If you think that the key to a healthy sex life is trying new things, then it is critical to know whether someone is willing to be open and share new sexual experiences with you, or if missionary is all that they are interested in trying.

#21 You have an extra $1000—what do you do with it? Would they spend it on you or them? Would they save it or spend it? This question will tell you if they are generous or stingy with their money.

#22 Would you go to a movie by yourself? How comfortable are they with themselves and being alone? People who are okay being by themselves are more comfortable in their skin and don’t need someone to make them happy. They want to have someone to make their life more meaningful, rather than fulfill a need.

#23 Do you like talking about politics? How open are they to different opinions? Do they judge people for what they believe? Often, someone who doesn’t want to engage in a touchy subject either gets too upset by conflict, or worries it will alter the way that they view you. It is important to be on the same political wavelength, but opinions change. Are they open to new ideas and discussing uncomfortable things?

#24 Did you hate any children growing up and why did you hate them? Were they the bully or the object of bullying? The playground is where we decide what behavior is acceptable, and what is not. What is unacceptable behavior to them?

#25 Has someone ever broken your heart? Are you going to be dealing with someone else’s baggage? If someone broke their heart, they are likely to have residual trust issues that will pop up in the future. It is important to find out if they have been let down, and how, so you know if they are likely to guard their heart.

#26 When do you think it is appropriate for a guy to cry? Is he a “guy’s guy,” or does she think crying is weak? This question tells you whether you can be yourself around someone and be as sensitive as you want to be. How much can you let your guard down and be who you are?

#27 Are your parents proud of you? Are they constantly feeling not good enough, or as if they let people down? Someone who is confident in their accomplishments will say that they have parents who are proud of them. It will also tell you how they were treated growing up, and if their parents fostered their emotional well-being.

#28 What do you want people to say and remember about you when you die? What is it that they value in human beings and hold as the epitome of what is important in a lifetime?

#29 How long do you think you are going to live? How optimistic are they about their life? If they believe they are going to die young, question them about why they have such low hopes for a long, happy future. Are they fatalistic, pessimistic, or even a hypochondriac?

#30 What makes your best friend your best friend? What are the qualities they think make someone a good friend, and what is it about their best friend that allows them to take that important role?

These deep questions are sometimes hard to ask, because we don’t really want to know the answers. If you are falling in love with someone, it is better to find out that they aren’t what you believed they were at the start, than to be blindsided in the end.