21 Questions To Ask A Guy Before Getting Into A Serious Relationship

Updated December 28, 2022by Regain Editorial Team

When you are casually dating, and you haven’t settled on one single guy for a relationship, what you are looking for in a guy could be entirely different than what you want for a long-term relationship, or what you have wanted in a past relationship. Your first crush, or the guy that you have the most fun with might not be the best relationship material. It can be hard to jump into a new relationship, especially if you've been heart broken or if you've never had a boyfriend or girlfriend before, but don't get discouraged or let past relationships get in the way. Break past the heart break- online therapy can help you break past it as well. 

Before getting into a serious relationship with someone you’ve been dating, prepare your questions to ask a guy on a date, or you should try these 21 deep questions to ask someone. These getting to know you questions are effective in helping you prior to dating to determine if you and your date are compatible or not. Here are some questions to ask a guy out during your date.

21 Questions to Ask a Guy

#1 Do you have my back no matter what?

Taking your relationship to the next level can be very scary, and you need to know that you can fully trust your partner. Ask them upfront if they have your back no matter what, even when they are mad at you or have issues. You may talk with them personally or through texting. How to talk to a guy over text can make you express your feelings more.. You need to know that thick and thin. Will they be there for you? Will they be your best friend? f you are looking for a boyfriend or a long-term relationship, could you see this person being your entire world?

#2 What do you consider cheating?

Different people have different views on cheating. Some women think that looking at a picture of someone of the opposite sex is cheating, or having a Facebook friend that is a woman could be cheating. In reality, these things should not be considered cheating because that would be indicative of controlling behavior. Yet cheating might mean different things to different people. One person might think sex is cheating, while someone else might consider a simple kiss cheating. You must be both on the same page from the get-go. Cheating is most people's biggest fear in a relationship, so it's important to have this established early on. 

#3 How much honesty do you feel needed in a relationship?

Not Sure If You Should Get Into A Serious Relationship?

Honesty is one of the most important characteristics of a boyfriend or girlfriend material. For a healthy relationship to work, you need to know that your partner is going to be honest with you no matter what. But at the same time, you don’t want someone who is going to be so brutally honest that they hurt your feelings all the time. Talk to your boyfriend about how much honesty they feel is needed and healthy.

#4 How do you think you’ve changed over the last few years?

Everyone should constantly be working toward being a better version of themselves. With every situation you face and every failed relationship you are in, you learn something more about yourself that you can use to improve yourself. Asking this question of a guy gives you some insight into how well they are in touch with themselves and their own needs and whether they are likely to evolve. 

#5 What do you want out of this relationship?

Make sure that you are both on the same page about where the relationship might go. Asking your guy what they want out of the relationship is your way to know what you might expect in the future. If you are marriage-minded and your boyfriend is not, you need to know that right away so that neither of you is wasting the other’s time.

#6 How do you deal with difficult situations?

It is important to know what coping skills your potential boyfriend might have for difficult situations that you might face. Couples go through all types of difficult situations, and at first, a lot of discussion and compromise is needed as you find your way through the muddy relationship waters. If your guy is quick to anger and has difficulty communicating during times of trouble, now is the time for you to know that to decide if it is a deal-breaker.

#7 Why didn’t your last relationship work out?

In some cases, the answer to this will be very straightforward, such as “she cheated on me.” But most often, when the first relationship fails, it is the fault of both parties, or it might have been just an incompatibility issue. An enlightened individual ready for a serious relationship will answer this question objectively and assume some responsibility.

#8 How did you deal with your emotions and feelings growing up?

This is an important question because the answer will tell you if you can expect your boyfriend to communicate their thoughts and emotions. The question also opens up an opportunity for your guy to show some growth by explaining the difference in how they now deal with emotions and feelings. You could even ask them about their most embarrassing moment as a child to make them vulnerable. 

#9 What do you personally think of your friends’ relationships?

The answer to this question will give you some valuable insight into what your boyfriend thinks of as a good relationship. They are likely to give you an example of a good relationship or an example of a bad relationship, or both if they know more than one married couple.

#10 Do you feel that we make each other better people?

The goal of any relationship is to be better together than you are apart. If you and your guy don’t make each other into better people, that negates part of the point of being in a relationship. If you and your guy bring out the worst in each other, a serious relationship probably isn’t a healthy choice.

#11 What do you value most about our relationship?

The answer to this question will give you an idea of how serious your guy is about taking your relationship to the next level. If they say something superficial like sex or having fun, you’ll know that you are wasting your time.

#12 Do you want kids?

Asking your guy if they want kids is an important question that you should ask before you get too serious. If you are marriage-minded and are looking for a life-long partner, you need to know if you are on the same page regarding kids, whether you want them or not. If you're already dating a man with kids, ask yourself if you're fine with that set-up.

#13 What things won’t you compromise on?

Everyone has deal-breakers that they will not compromise on. You and your partner need to discuss your deal breakers and make sure you are both on the same page. If something is black and white and you can’t agree, now is the time to discover that instead of years down the road when it counts.

#14 Will your parents and friends be a problem?

Sometimes guys have a toxic family, or they have nosy friends against them being in a serious relationship for whatever reason. You must know what you are getting yourself into before it starts. Asking this question ensures there are no surprises, and you can decide if it’s worth it.

#15 What are your top priorities?

It’s really up to you what you consider to be a reasonable answer to this question. Most guys are going to say career, money, and you. If you are not one of their top priorities, you are wasting your time. Of course, they should make themselves a priority as well, but you should be up toward the top of the list.

#16 What are your views on women?

If you have been in a casual dating, you may not know your guy’s views on women. Some guys can come off as very nice but be very chauvinistic in their behavior and attitudes. You need to make sure that their views on women do not conflict with your female empowerment views.

#17 How important is sex to you?

For some guys, sex is extremely important, and without it, they are not going to be happy in the relationship. If this is the case, you need to know that going in so that you can decide if that is something you are willing to give into. Some women are perfectly okay with having very frequent sex, but others are not, and you need to make sure you’re on the same page.

#18 What are your religious and political views?

When you first start dating someone, you want to avoid topics about religion and politics because you want to get to know each other without these controversial subjects getting in the way. The difference in religious and political views are dating deal breakers to some people. But if you plan on taking your relationship to the next level, you and your guy need to either be on the same page or be able to agree to disagree.

#19 Do independent women scare you?

If you are an independent woman and don’t rely on a man, you need to be upfront about that to your boyfriend and allow him to back out. Asking this question lets you know if your guy can handle a serious relationship with a strong woman.

#20 How is your financial situation?

Not Sure If You Should Get Into A Serious Relationship?

No one wants to talk about money, but if you are in a serious relationship with someone, you need to have some idea of their financial stability. The last thing you want is to get into a relationship with someone who is not financially stable and relies on you for everything.

#21 Are you open to relationship counseling?

Throughout a relationship, there are many different times you might need to see a relationship counselor. If you or your partner go through a major life event, when you take your relationship to the next level, such as moving in or getting married, or when you have problems in and out of the bedroom, a willingness to seek relationship counseling can save a relationship.

You must know upfront if your partner will be willing to go through relationship counseling. In fact, experts say that you should go through relationship counseling before getting married or taking on a life partner because you will have a much higher rate of success in your relationship.

If your guy answered these 21 dating questions satisfactorily and you are ready to take your relationship to the next level, relationship counseling can help prepare both of you for a successful relationship.

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Before starting a relationship, it is unquestionably vital to ask yourself these 21 serious questions to fall in love. However, it's also fun to learn about someone by asking questions like, what's your dream job? Biggest regret? Dream vacation? Dog person or cat person? Favorite food or one food you couldn't live without? Morning person or night person? Favorite fictional character? Most treasured memory? Favorite family memory? What would you do with a million dollars? What is the craziest thing that has happened to you? What is the biggest lie you have told? 

These questions are fun and tell you a little more about a persons personality, values and likes.

Below are commonly asked questions on this topic:

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What's a good flirty question?
What are 21 flirty questions to ask a guy?
What are some juicy 21 questions?
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What talk about with a boy?
How do you test a man?
What is the deepest question to ask a guy?
What are some serious questions to ask a guy?
What questions do guys like to be asked?
What to ask a guy to know if he’s serious?
What are some dark questions?
What are juicy questions to ask a guy? Should I date him?
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