Home Featured The Five Essential Questions You Need to Know About Your Relationship

The Five Essential Questions You Need to Know About Your Relationship


Some of the strongest romantic connections are spontaneous, start fast and move very quickly to falling in love. However, when you’re falling in love, you’re likely not worrying about the important issues that when they come up later can be a recipe for disaster. I’ve always gone back and forth with questions that you should ask and when you should ask them. Most of the questions that I’m going to list here in this post aren’t first-date questions; it’s probably way too invasive. When I’m talking to someone about their relationship, I’m always certain to figure out if they know the answers to these questions. I think there are just certain things that you guys should know about each other.

What are you like when you get upset?

Every couple should spend time figuring out what happens when their significant other is upset. What are those things that upset them and how they react are essential questions that need to be answered. There are two types of people in this world, there’s those who outwardly express their anger and those who hold it in. Personally, I’ve found over the years that I typically deal with most of my anger on the inside. Therefore, somewhere along the way my significant other will have no clue that something they do bothers me. I deal with being upset by distancing myself from the problem and reducing its ability to affect me. If your dating someone like this, it’s critical that you have a conversation so that you both know how to go forward.

When to ask: Right before you make the relationship official.

What exactly happened in your last relationship?

Everybody has things they don’t want to talk about and that’s fine. Your last relationship is not one of those things that you can really hold onto yourself because it really affects your next relationship. That’s why you have to have this conversation at some point. It doesn’t need to happen early on but at some point you have to be careful having the conversation. You need to know if they were cheated on or cheated in their last relationship, which may be an indication of trust issues that may have developed. You need to know if they dated someone who was abusive or too submissive; it’s an indication of the person you’re inheriting. If they’ve never been in a relationship before… well, good luck.

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When to ask: Once you’ve decided to exclusively date.

What do you like in the bedroom?

You know how bad sex happens? Because couples aren’t talking about it. I do not have a clue why you would subject yourself to that. It’s deeper than just bad sex because the sex may be “okay” but even that is still wack. Here’s why you want to talk about this; if you don’t then there will be a gap between what is desired and what is provided. Listen fellas, if your girl wants to be treated like a dirty, disgusting and filthy whore in the bedroom, do that ish or someone else will. Ladies, if you go on your man’s computer and you see that the videos that he watches on those adult sites are not happening in your bedroom, “you got problems.” Let me be clear, I’m not saying that people should get out of character in the bedroom but they should be aware of what’s wanted.

When to ask: After about the tenth time you’ve had sex.

How does your family and friends affect your relationships?

Short answer is they shouldn’t affect it. Real answer, they have a significant impact on your relationship and you need to discuss it. Setting aside daddy and mommy issues, there’s other ways that your family can shape your relationship. For example, what if there’s no strong emphasis on marriage before children in their family? What if they’re a child of divorce? All questions that can affect your relationship. Also, friends play a big part too. I’ve dated women who’s friends were all single and all negative as hell about men. I had to know that when she went to her friends with issues in her relationship, they would likely be the conspiracy theorists. I know for men, if your friends are all single and living that single life, it can really affect your relationship. You need a support system. If your boys are heading to happy hour but you’re on duty with cutie, after a while that can weigh on you. Are his boys the type to say, “Man you need to go spend time with Big Shirley” or “That’s why we told you not to get in a relationship”?

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When to ask: A month or so into the relationship when you’ve made it past the awkward newbie phase.

What are your views on long term commitment and what does that mean?

Listen here, people don’t ask this question and they end up wasting years of their lives in situations with people they love but in the long run don’t work out. You need to know early on if there’s no real future with this person. How long do they see themselves dating a person before marriage? If not a time, then are there certain checkpoints that will let you guys know when you’re wasting your time? Does a long term commitment also come with the expectation of cohabitation? Is the relationship seasonal with an expiration date when one of your moves away in a few months? These are all important questions that need to be answered. The worst feeling is when you fall in love with a person, like really truly love them, but in the end there’s just no feasible way you can be together for a long period of time.

When to ask: 3-6 months, after your first argument or disagreement.

Those are my five, I’m sure there are more and you’re welcome to share them in the comments section one time. I heard a girl joke that when she got married there were all these questions she never thought to ask but became critical once they were under the same roof in a lifetime commitment. “Do you like creamy or chunky peanut butter?” “Do you like toilet paper rolling from the top or bottom?” “Dishes washed immediately after dinner or after a bit of time to relax?” Yeah… funny yet pertinent questions because over of the course of time those things will lead to annoyance and unnecessary arguments. Have the conversation early and avoid it being awkward and uncomfortable later.

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– Dr. J


  1. Probably putting myself out there but…
    "If they’ve never been in a relationship before… well, good luck." <—– What would this indicate? (i.e. What would this mean to a guy if a girl has never been in a relationship before?)

    1. It's not a hex. It's more like something that a person should be aware of. It's not impossible to deal with someone who's never been in a relationship before. I think it just means that you're going to have to be more patient than in other situations. On the flip side, sometimes people been in so many relationships that their conditioning has been conditioned. In the case of the person who has never been in one, it's risky, but it can be done. The person just doesn't have any real idea of what being in a relationship is like…

  2. Good points J. I would also add that if you are looking at a long term relationship with this person and see a future, gotta ask about that financial history also. I understand people experience hard times in life, but if you not working on fixing those credit score issues(and other financial shenanigans), but still up at Bloomingdales getting that new Prada purse, we have issues….Just sayin though…

  3. About the bedroom… Don't allow yourself to have 10 times some bad-okay-sex!!! It's too many times :O! If the 1st time wasn't as good as you expected it to be, talk about it right away and it will only improve, don't waste time!!!

    1. I mean… the only reason why I said ten is because you can't tell somebody after you have sex a couple times… "really what i'm into is S&M, so if the next time you could tie me up and leave me outside the door that would be great, k thanks!"

      1. Ya, I think it depends on what needs to be said. More extreme fantasies should wait a bit of time. But some of the more simple things could be coached even on the first time. Regardless of when it’s said though, it’s more about how it’s brought up. Sharing your body with someone is a vulnerable place to be….so when someone says they don’t enjoy it, some egos can be bruised.

      2. Shouldn't you talk about sex before you have it???? By the fifth time the person your dating could assume your into 3somes, (because they are) or that you may be bisexual because they are or because you seem very open-minded or that your into S&M because your cool with being smacked on the azz and having hot candle wax drizzled on your naked body….ijs.
        I think when you don't have a convo prior to having sex it can make for some awkward moments. Think Along Came Polly when Ben Stiller smacked Jen Anniston on the azz following the advice of his crazy wannabe movie star friend who was single as a dollar bill.

  4. I think this list is pretty good. I would probably ask the “How do you show you’re upset?” question a little earlier than before you decide to make it official only because even though those beginning stages are normally all googoo eyes and ish, I still think it’s important to know a little earlier. Not first date early, but a little earlier than right before making it official.

    I also was just hearing about this book called “The 5 Love Languages” and I think it’s important to ask someone a variation of, basically, how do you show someone your love? For instance, I’m a person who likes words of affirmation. I like you to TELL me how you feel about me… But if you’re a person who only does “acts of service” and only shows your love through what you DO for that person, but can’t verbalize who you feel about the person… Then a communication issue can arise because your expression of love is different than how the other person may desire. Now, I don’t know WHEN you ask that, but it’s still important to find out.

    1. Good point about the "The 5 Love Languages." Definitely a good tool to use to understand how people express themselves to their significant other. I recently discovered this a few months ago and my profile definitely described me accurately.

      1. That's a really good, and short read. But, I think someones "love language" is really significant to overall success in a relationship. After I read the book, I found myself more observation to what women really want, cause it can be frustrating to not know what a person values. So, I think this brings up another good question, "how do you show love/appreciation for someone?" This would be nice to have a mutual understanding that my partner shows love this way.

    1. I don't think that's a question for a relationship but more a question for a marriage. It's not really required information that someone knows that i'm working to improve my credit or that I have a six figure stock portfolio i'm just sitting on. Most times, when people think about discussing $$ views it's about the negative and not the positive. But when you look at it the other way around I think it becomes more clear. What if I don't want the person i'm dating to know exactly how much i'm sitting on?

      1. I agree. The only downside to that is not knowing where your spending limits are. It's kind of hard to suggest things to do when you don't generally know where their finances are.

  5. These are all good, I just don't agree with the timeframes. I think depending on what you want these should be asked fairly early on.
    What you don't want to happen is you fall madly in love with a person after being in a serious relationship with them for 6 months, and you envision yourself spending your life with them. You ask them all these questions and they tell you what you want to hear so they don't lose you, or your already half a year deep into them and you let stuff slide because you really like them and you've gotten attached to them. I think if anything these are questions you ask after you've dated for a while when your ready to actually be in a relationship.
    The most important thing is asking all the questions that are important to you so your relatively happy and satisfied in your relationship. The other important thing is knowing where you stand with that person and ensuring that your both on the same page and want the same things in the same timeframe.
    Granted I don't think you need to know the financial history of a person your casually dating, but you should know before your at the point where your ready to propose.

  6. Magnificent web site. Plenty of helpful info here.
    I am sending it to several pals ans also sharing in
    delicious. And certainly, thank you in your sweat!


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