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

Updated August 03, 2021

Medically Reviewed By: Lauren Guilbeault

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. The guy that you have the most fun with might not be the best relationship material. Before jumping into a serious relationship with someone you’ve been dating, you should ask these 21 questions.

#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 need to know that thick and thin. They will be there for you.

#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.

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

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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 a 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.

#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?

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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.

#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 dating casually, 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. 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?

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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 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. If you want affordable and convenient online relationship counseling, ReGain is available by a smart device with a data or internet connection any time of the day or night.

Counselor Reviews

“With Cassandra’s help, we’ve been able to bring our relationship to a new, healthier, and much happier level, working through painful situations, growing as individuals and as a couple, and with tools to stay on this path. She’s very responsive, and it has been great to have her facilitate our messaging through the app all week. I highly recommend Cassandra. She’s skilled, supportive, and down-to-earth. We feel totally comfortable with her.”

“Sessions with Natalie are very insightful and give practical advice on implementing new habits and changes. Be prepared to engage and be challenged to think in a different way. I know that my partner and I can already see improvements in our relationship and feel more positive about working through our issues together.”


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