Before Going Further: 30 Deep Questions to Ask Your Boyfriend

By: Julie Keating

Why do we all save the really deep questions to ask your boyfriend for well after committing to them? Talk about these questions early on instead.

There are many things we keep hidden during the beginning of a relationship. The problem is, these things we keep from our significant others are typically the things haunting the relationship later on. If you hide the crazy too long, and then let it all out at once, it is nothing but, well, crazy. And these deep questions to ask your boyfriend can help you avoid that.

Being yourself is key to any successful union, including being honest and asking uncomfortable questions. If you get to a point in your relationship where things are getting serious, proceed with caution. Those things that you think are not such a big deal become a major kink in the relationship chain if not addressed early on.

All those little voices in your head making you question things they do and whether it will be an issue later are there for a reason. Yes, they will be a problem, especially if you don’t clear the air by asking those deep questions no one really wants to ask.

30 deep questions to ask your boyfriend

The problem in most relationships is that we are afraid to ask intimate questions upfront for fear we’ll make someone uncomfortable or send them a message that we are moving too quickly. When you don’t ask the important questions, you run the risk of falling in love with someone who isn’t right for you.

These are the 30 deep questions to ask your boyfriend. Uncomfortable, yes, but necessary to take things to the next level with trust and honesty.

#1 Are there things you have done in your past I should know about? The last thing you want to do is to run into someone from their past to find out that they were the biggest player that ever lived, or that they spent time in “juvie.” Giving them the floor to make any confessions about their past ensures you never get blindsided.

#2 What type of guy were you before you met me?  Is he the serial monogamous, or the sleep with anything type of guy? You may have changed him, but it is nice to know who he was before you turned his eye.

#3 What are your old girlfriends like? Are you his “type”? Knowing what his other girlfriends were like might give you a perspective about what he looks for in a girl, and what it was about the other relationships that didn’t work, and this could help you avoid making the same mistakes.

#4 What broke up your previous relationships? Sometimes, there are deal breakers a guy won’t come right out and tell you about. By learning what broke up his old relationship, it provides you insight into whether he has been hurt, cheated on, or if there was something that simply wouldn’t do for a relationship to move forward.

#5 Have you been in love before? Knowing whether he thinks he has been in love before tells you whether he has the emotional maturity to get in touch with his feelings. You have to have something to compare your feelings to, and if he hasn’t ever been in love, then how does he know what love is or when to recognize it. [Read:

#6 Who was the first girl to break your heart and how did she do it? We all have baggage in our past. Knowing what is in his issue suitcase helps you navigate difficult times with him, avoid triggers like trust problems, and even reassure him that you aren’t his ex, nor would you ever do what she did.

#7 What’s your five-year plan? Does his five-year plan involve a family and wife, or is it all about his career? Guys who have plans rarely veer from them, so knowing what his intentions are up front, is the best way to find out how you will fit into them. Or if you will at all.

#8 Do you like children, and do you want to have them? Women typically put off this question because we fear scaring the guy off and make them think our biological clock is ticking. The truth is that no relationship is going to be healthy if you want different things out of life and children are about the biggest change a relationship goes through.

There are some who absolutely can’t live with them and those who can’t live without. Just make sure you are on the same page before falling in love.  [

#9 What is your biggest pet peeve? Those little things we do to irritate each other at the start don’t seem that big, but after time, they become deal breakers. Find out what his biggest pet peeve is so you know if it is something inherent in you or something you are capable of avoiding.

#10 What is a relationship deal breaker to you? What is it that he simply can’t live with in a relationship?

#11 Do you think divorce is okay? When you get married no one ever thinks they will get divorced, but there are some with a greater commitment to seeing it through. While others think if it isn’t going so well, divorce is a way out. It is important you both are on the same level of marriage commitment.

#12 If you do have children, is it important what religion they are raised?Even if he doesn’t attend mass, the religion he raises his children may be very important to him. And, if you aren’t the same, that could pose some serious problems not just for you two, but your families as well.

#13 What are your political beliefs? Politics are something people avoid because it tells a lot about who someone is. If he is ultra-conservative and you are a bra-burning liberal, being together is going to be pretty difficult without strife. You just see the world through a very different lens.

#14 What do you think about prejudice? We all hide our prejudice when we start dating for fear of judgment, but if he has some serious prejudices against some group or religion, that is something you may want to know before you hear the ugly later on.

#15 Do you think family is important? How important is his family in his life? Is it your family first, or the peripheral family, that guide his decisions?

#16 Who comes first, your wife or your mother? Mothers can ruin even the most excellent relationships. Know where he would stand, and who’s side he would take, before she becomes your biggest nightmare.

#17 Do you expect your wife to stay home or go to work? Does he believe in traditional roles or does he want you to share in the financial responsibility?

#18 Will you keep your finances separate? He shares his bed, but not his finances. That says a lot about the level of intimacy and closeness he wants to have with his significant other.

#19 If you were in trouble would you hide it from your wife? Is your wife your confidant or is she just an accessory? If you want to marry someone who you tell everything to, but he wants to keep things to himself, that creates issues of closeness and feeling like he hides things. It is a very complex road to go down.

#20 What is more important your job or little league? Is he into raising his kids or is it business at all costs? If you don’t want to be sitting on the bench alone forever, it is important to know whether he is going to want to take a part in it all.

#21 Are you a saver or a spender? If you are a saver, and he has credit card debt that is out of control, that can create huge problems for you two. Make sure you are on the same financial page to avoid potential problems in the future. [Read: How to make a relationship last: 19 love commandments]

#22 How strict were your parents? We tend to parent the way we were parented or go completely the opposite. How did his parents raise him and does he think that it was the right way or the complete wrong way?

#23 Do you believe major decisions should be made together? Is he going to come home with a Porsche one day, draining your savings account just because he felt like he needed an impulse buy, or does he think he should discuss it with you?

#24 Would you be honest even if you knew it would hurt my feelings? If his feelings changed or something serious was going on, would he be honest even if it isn’t comfortable or something anyone wants to talk about?

#25 Would you ever look at my phone or through my personal things? If he starts spying, you will too, and then the trust slowly gets chipped away.

#26 What do you remember your parents fighting about? Were his parents disconnected, fighters, or good communicators? You tend to do what you grew up with, so knowing how his parents related is a good indication of how he will communicate with you.

#27 What type of relationship did your parents have? Is he from a broken home or a Betty Crocker one? This gives you an idea about his perspective of what a family is supposed to be.

#28 Would you say you were you closer with your mom or your dad? Did he hang out with his dad in the garage or stick by his mom’s side? If it was his mom, be careful he may just be a momma’s boy.

#29 What is a tradition in your family that you absolutely have to keep? If going skiing every Christmas is just what he does; then those are the things you need to know because you will be doing them forever if things last.

#30 Would you be okay if your wife was more successful than you monetarily? How comfortable is he with letting you shine even if it makes his star not so bright all the time?

The key to a healthy relationship is being honest. And, if you can’t be honest at the beginning, what makes you think things will get better? By the time you feel comfortable asking the most important questions, you will be in love, and it will be too late.

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