Serious Questions to Ask Your Boyfriend: Common Interests

It’s important to ask your boyfriend what his long term goals are, because ultimately, if your goals are conflicting, you need to consider where your relationship is headed. However, before you ask these questions, think about your own answer to them so you can see how much you have in common.

Remember, goals and opinions do change over time so you do not have to be a perfect match. It is up to you to decide what is worth compromising on and what viewpoints are not compatible.

Try not to be aggressive when you ask serious questions. You tone of voice and approach can make a very big difference when having serious conversations. Also, be patient if he needs time to think about the answers and can’t give you a direct answer. Don’t throw a good relationship out the window because someone doesn’t have their entire life mapped out.

The good news is, this exercise will probably strengthen your relationship rather than harm it. When you start to realize how much you actually have in common, it can really strengthen the bond between you. We’ve prepared some serious questions to ask your boyfriend which can reveal a lot about your compatibility.

1. Does he want kids?

This is one of the most obvious serious questions in a relationship. Perhaps one of you or both of you are unsure. That is ok and don’t force yourself to figure this out right away. However, if one person is adamantly opposed to the concept and one person has only ever dreamed of having a family their whole life, it is important to discuss and weigh when considering a long term relationship.

Here is the next part of the question. How many kids does he want? If one of you wants a big family but one of you wants a micro family, that is something you need to address. It’s challenging to debate things that haven’t happened and plan based on them but it is valuable, after all, it’s our lives we are talking about here.

Remember, just because two people get along and are good people doesn’t mean their goals will align. Sometimes they are better off as friends.

2. What type of lifestyle does he want?

Lifestyle is a vague term, but it mostly refers to one thing, money. If he wants to live a luxurious lifestyle and you like the idea of a shack by the beach, you might not be seeing eye to eye. Alternatively, if you dream of a home in Beverly Hills, and he’d rather enjoy the simple pleasures of life in a Cabin in Maine, you might be a city slicker dating a cowboy.

Often when people are first attracted to each other, it takes some time to determine if their desired lifestyles align at all. This is important because it dictates how you both want to spend your time and what your career goals are.

Are you a minimalist dating a materialist? You can often determine these things based on how you dress. If you’re a thrifter and he only wears Seven Jeans and True Religion, you might not be a match made in heaven. It’s important to call a spade a spade, no matter how much you might be attracted to someone or enjoy their company.

If you have fundamentally different lifestyles, it’s going to be hard down the road. It’s hard to face things like this but if you put it off now, you’ll have to face it later on. If you like camping and he prefers The Ritz, do you think you might be forcing it? Lifestyles are rather important and shouldn’t be swept under the rug by any means.

3. What are his political beliefs?

That sticky and loaded question! Well it is still important and should not be avoided. Down the road, if you plan to combine your finances and you want to contribute to a republican candidate but he is a libertarian, you’re going to end up in a conundrum.

Some people are agnostic when it comes to politics and couldn’t care less. If you plan on being very involved politically and it’s a big part of your life, it might be hard to be with someone who doesn’t care one way or the other.

If you are someone who likes to debate current events and votes in every election, it might be challenging to be with someone who doesn’t know the difference between the primaries and primary school.

4. How does he like to spend his free time?

This is a pretty specific question. Let’s say he loves spending time with his friends every day. They play video games and drink beer every night until 2am, blasting Metallica. Would you like that? You don’t want to try to change people, right? Chances are this won’t be that much of a bone of contention, but sometimes it can be.

If nothing else, it may help you bring some balance into your relationship if you think about how you are both using your time. Maybe you need to spend more time with friends, exercising or on dates. It gives you both an opportunity to check in and voice your opinion.

5. Is he the marriage type?

Maybe he is the marriage type and you’re not. You wouldn’t want to hurt his feelings two years from now, and break that news to him. It’s not important to decide right now if you’re going to get married, because chances are you couldn’t possibly know, but if you have completely different views on the subject, it might raise a red flag.

Many partnerships are completely healthy and happy without the marriage license. Try to approach these questions with an open mind and it can be valuable, if you really care about the other person, to try to understand their viewpoint.

6. Has he had a long-term relationship?

If you are looking for a relationship, and he’s never hung out with someone for more than a few weeks, you might be barking up the wrong tree. This happens to both men and women though. Sometimes men are the ones serious about getting into a relationship and the women are thinking less seriously.

In order to be sensitive to both people, it’s an important conversation that adults and mature people should have. If your partner refuses to talk about it, then he is just acting childish and is not worth your time .

It’s up to you to decide if you want to have a relationship with someone no matter what their history. If someone has changed, they may end up being a great lifelong partner. On the other hand, if you are looking for a relationship that is not too serious and he is looking for the one, you may feel pressured. It’s just as important to be clear with what you want as it is to know what he wants.

7. Is there something significant in his past you need to know?

How do you ask a person a question like this without judging them? Try to understand what their life circumstances were and what they were dealing with. If you are dating a convicted felon and you don’t know, you might as well ask upfront instead of being surprised down the road.

It’s important that people are not naive in relationships and that goes for both men and women. Asking questions upfront keeps relationships transparent, and you can avoid potential arguments in the future. Open communication is essential for any healthy relationship.

8. How does he eat?

To some people, this may sound like a silly question, but with the many varieties of food preferences, it’s actually more important than most people think. If you are a meat lover and he is a vegan, will you be able to eat out together? Will you be able to enjoy food? Is one person willing to sacrifice their habits to accommodate the other person? These are important hurdles to overcome in a mature relationship.

I’m not saying differences in dietary preferences are insurmountable but they can be a point of contention. It’s also important to take note of how long a person has been eating the way they are to determine if it’s a passing trend or a lifestyle choice that will probably stick.

9. What are his long term goals?

Ah, the question that dwarfs all other questions: the ten year plan. Have you ever been asked this question and felt completely unprepared, because you were still debating what you were going to do this evening, and couldn’t quite focus on ten years from now? It’s as if your entire future hangs on this one question.

It’s important to be honest, maybe you’re working on it, or you need to sit down and evaluate your priorities. Sometimes it can be hard enough managing day to day challenges, so long term goals get the back burner for a while. Many people haven’t thought this through all the way.

Everyone will answer this question differently, and it is not something that is set in stone. It’s just a gauge to see how much your priorities meet his, and if they are somewhat compatible. It’s good to have different goals; you are two separate people after all. But knowing the direction you are headed, and being aware of his, can really help to shape the way you use your time and think about how you spend your money.

10. Where does he want to live?

This is another one of those questions that will have different answers depending on when you ask. Most people aren’t exactly sure, so don’t demand an answer. This is important though, because first of all, some people really want to get a house and settle down, other people loathe the idea of a mortgage, and want the freedom of renting.

Many times this comes down to other goals such as having a family or focusing on a career. Career goals can also play a big factor in where someone wants to or will need to live. If you are dating someone that is going to have to move to Texas, that is probably something you want to know, right?

When asking serious questions, keep an open mind, you never know what the future holds, no matter how sure you are of your plan. If you are with someone who is goodhearted and treats you well, there are a lot of differences you can overcome.

I have seen couples change their minds from not wanting to have kids to being happy parents. I have seen people take 10 years to decide if they wanted to get married. Patience and putting yourself in the other person’s shoes can mean the difference between breaking up and a lifetime together.

I can’t resist encouraging you to ask these questions early on. If you scare your boy off, then he really is just a boy. A man can have these discussions openly and candidly without being thrown off or getting freaked out. Remember, just as it is hard for you to make up your mind about your career, where to live and how much financial strain to take on, he deals with the same confusion.

Life isn’t always cut and dry like a haircut, it’s messy and we need to recognize that we are doing our best. If two people are doing their best and working on things, that helps to strengthen their relationship. If you aren’t able to see eye to eye on too many of your goals, it may be time to reevaluate your relationship.

Imagine how much time you could save if you were upfront and direct about what is most important in your life right off the bat. Historically, women have put their dreams aside when they met a man they fell in love with, but in the age of equality, we must seek a balance. If we only focus on our career goals, we may live very lonely lives.

For some people, being a spinster isn’t all that bad. If you want both, compromise and find a common ground. Remain optimistic in your quest for a successful career and a healthy relationship, because when it all boils down to it, attitude is everything.

A positive attitude can make things happen and a pessimistic attitude can lead you to only see what could go wrong. Maintain your positive outlook and push through minor panic attacks if you want something to last.