15 Questions You Need to Ask When Dating

15 Questions You Need to Ask When Dating | AllGroanUp.com

Is this “The ONE?”

When I was dating I remember constantly being smothered with that giant question like a bloated bear was sitting on my head, refusing to move.

How do you find The ONE? That’s the point of dating right?

To magically stumble upon The One like finding the gold at the end of a rainbow that is being carried by a unicorn with leprechaun jockey.

But how are you supposed to know which “One’ is the right one? 

How are you supposed to lasso that magical unicorn before it flies away?

Well, if you’re dating someone, or thinking of dating someone, here are the 15 crucial questions you need to be asking you and your dating relationship.

15 Questions You Need to Ask When Dating | AllGroanUp.com

Original Photo by Leland Francisco

1. Do I want to become like this person?

Marriage is like rolling Play-Doh, the more two different colors are meshed together the harder it becomes to distinguish one from another.

In marriage you begin to rub off on each other, subtly taking on traits and characteristics of the other.

Does this thought excite you or does it make you feel like you just digested a can of the before mentioned Play-Doh?

Yes in marriage you still are your own person. And you need to have your own identity beyond your spouse. But…

If you don’t want to become like the person you’re dating, should you be dating?

2. Am I attracted to this person? (and do I realize that attraction runs much deeper than looks)

One of the biggest lies of our culture is that attraction is solely about appearance. (Tweet That)

If you can just get your hair, abs, complexion, and clothes just right, then The One will scamper to you like a squirrel to a nut factory.

However, attraction runs much deeper than looks. Sure appearance might catch someone’s eye, but it’s personality, values, faith, heart, past, present, and future that’s going to make them stay.

Your petals might be beautiful, but if you don’t have any nectar then the bees are just going to fly away.

Finding your spouse attractive is much more profound than thinking they’re smoking hot.

3. Have I let physical intimacy blind me of what’s really going on underneath?

Is your physical intimacy greatly outpacing everything else?

As I wrote in 3 Things Love IS NOT, “Sex is not love.”

Sex can be a liar. It can prop up an intimacy that has no foundation to sustain it.

Letting physical intimacy run wild and free typically means the emotional, spiritual, and personality attraction is lagging behind. And unsuccessfully trying to catch up.

Sex while dating can create many awful shades of gray, when what your relationship needs is some honest black and white.

4. Do our core values and beliefs repel or compel each other?

One of the greatest causes for conflict in marriage are contradicting core values.

I’d describe core values as beliefs that are fundamental to how you are wired, guiding your actions, thoughts, plans, and purpose on this earth.

We all have values that direct us and help us make decisions – problem is most of us have never articulated what those values are.

And if you don’t know your values, how can you expect your partner to have a clue?

Not all values are the same and sometimes you can have two very good people with very good values, but those values can feel at war with each other.

As I wrote in 5 Musts to Look For in a Spouse: “If your core values can’t dance together, then you’ll keep tripping, falling and wondering why you can’t move together in rhythm.” 

For example, you could have a high value for responsibility and the person you’re dating could have a high value for risk. Both values are good, but if not articulated and discussed it could be a point of high conflict if the responsible person likes consistency and persistence, while the risk-taker likes changing things up and going for the impossible.

Take me for example, one of my core values is authenticity. I struggle being in a job, friendship, situations, etc. where I feel like I’m having to pretend to be someone else. It makes me feel anxious and that I’m lying.

How this plays out in my life, especially in the aspect of career, is that I struggle doing work I don’t believe in and isn’t aligned with who I am. Authenticity forces me to intensely evaluate why I’m doing what I’m doing and strive to do work aligned with my beliefs. Thus my career path has been anything but straight-forward, which could drive any sane person crazy.

Thankfully, my wife has been very supportive because she knew this was the way I was wired from the beginning and it aligns with her core beliefs, as she enjoys change and pursuing things off the beaten path.

Too many marriages start (and end) with vague and un-identified core values.

5. Do I like who I am when I’m with him/her?

Are you really being you when you’re with them?

Or are you constantly trying to hide who you are because they want you to be someone you’re not?

Are you fitting and conforming to some abstract idea of what you think they want? Or are you blossoming and flourishing into who you really are?

Do you feel fragmented when you’re with your partner or do you feel whole? 

Which leads into Question 6….

6. Does this person challenge me to be a better, authentic version of myself?

Is your partner trying to force you to become like some figment of their unrealistic dating imagination? Or are they challenging you to become a better, authentic you? Not trying to change you, but trying to bring the best to the top.

A spouse should be like a gold miner, going under the surface to uncover the invaluable stuff underneath.

Is the person you’re dating like a magnet trying to bring the best of you to the surface?

Or are they trying to bury you under a pile of dirt?

7. How does their family communicate? (And am I comfortable if this person begins to communicate with me in the same way?)

We all go through intense communication training for years; it’s called childhood. (Click to tweet)

And it’s hard to un-wire 18 years of being shown how to talk and listen to others in family situations.

Sure we’re not our parents and we can work to change our communication habits. However, for many of us our fallback communication plan will be the one our parents laid out for us.

Holidays, especially, are giving you a glimpse into how your partner has been taught and trained. Don’t just sit back and eat that holiday ham. Sit up, take notes, because believe me you’ll want to feel prepared for the test that comes later.

And the test will come like a train on a dark and stormy night! I promise.

8. Do they love from their insecurities or do they love from their strengths?

I first asked this question in 11 Questions Every Twentysomething Needs to Ask, and I think it boils down to this: Is their love based on YOU or is their love based on THEM?

Does their love demand? Or does there love give?

Love can be the worst form of manipulation there is. 

Your partner can look and smell like a rose, and yet continue to prick you with their sharpened barbs.

Does your partner seek out ways to understand how you receive love and meet that need? Do you do the same?

If you or the person you’re dating loves out of their insecurities, their love will be needy and selfish.

When someone loves from their strengths they know who they are and are drawing from a deep, full well to give to you without demanding a drink in return.

9. How does my partner handle money?

Is your partner a saver or a spender? Do they budget?

Are they willing to honestly talk about money at all or is the topic taboo?

Honestly, going into marriage with my wife I really struggled talking about money. When the topic came up I’d usually become defensive because I wasn’t making too much of the stuff.

I let money and the honest conversations about it become a wedge in my relationship. And I’m still learning that it’s not a topic to be avoided, but embraced.

Conversations about money can be the great time bomb in a relationship. Uncover it now before it detonates. (tweet that)

10. What are both of your non-negotiables?

When you think about your future together, can you list three things that you think would be excruciating to let go?

For example, maybe you know without a doubt that you want to have kids. Or that you don’t.

Maybe leaving your home state and your family feels like an impossibility.

Maybe you never want to work a standard 8-5 job in a cubicle.

As you mature and grow into life, sometimes our non-negotiables morph and tweak. But I do think having you and your partner list out three things you don’t want to ever budge on is a good conversation to have. Identify what you feel are non-negotiables now so you can avoid any large, gaping ravines ahead.

11. How important is faith to me and faith to them?

Does religious faith play a role in your present and do you want faith to play a role in your future?

What do you truly believe about how to live your life and what happens when you die? Weighty questions, I know, but important ones. I really believe that if there are large differences in your faith now, those will only become bigger and more cumbersome as your relationship progresses. Especially when kids come into the equation. How will you raise them? What do you want them to believe? Talk about it.

12 . Have you both tackled your monsters?

We all have insecurities, fears, failures, painful memories, and just all around unattractive stuff we’re hiding in the back of our closest.

Like that yearbook from our awkward years, we all have things we hope our partner will never lay eyes on.


Just because you want to pretend your monsters don’t exist, doesn’t mean they’re just going to magically go away.

And marriage has the amazing ability to take all that you hoped remained hidden, and put it on stage for a nationally televised interview that your in-laws will be watching.

Tackle your monsters now. Don’t let them crush your relationship later.

As I wrote in my book 101 Secrets for your Twenties,

Newly married and living in a small apartment is no place to store a luggage set full of your baggageBegin to ditch those bags now.

Right attracts right. And the more right you are, the more right your relationship will be.

13. Do we enjoy doing the mundane together?

Marriage is as every day as it gets. 

Marriage is budgets, laundry, broken toilets, work, weddings, funerals, births, and everything in between.

Can you envision enjoying every day life with the person you’re dating?

Again as I wrote in 101 Secrets for your Twenties,

If you don’t enjoy going to the grocery store with this person to buy eggs or changing the clothes at the laundromat, then you might not enjoy doing marriage. Because marriage is built on a million more mundane moments than magical.

14. What’s their vision for the future? Kids? Careers? Travel?

How do you envision marriage after 10 years? Are you traveling the world with your spouse? Do you have three kids encased in white picket glory? Are you both working corporate jobs? Are you doing missions work in a different country? Do you have six kids and are driving a bus across the nation to perform a family rhythmic gymnastics routine at county fairs?

Your plans, goals, and ideas of the future change–but people who refuse to talk about it rarely do.

15. (Bonus Points) Can you write a vision statement for you and your relationship together?

Now not many couples do this ever, whether dating or married, so this is definitely Advanced Relationship 101. But with what you know now after going through these questions, can you sit down together and write a vision statement for your relationship?

What will be the goal of your relationship beyond just your relationship? Who and what will you impact together?


Find more crucial questions about dating, marriage, and living a purposeful life in my new book 101 Questions You Need to Ask in Your Twenties. 

Written in the same easy-to-read style and humor as my best-selling book 101 Secrets For Your Twenties, but this time we’re digging deeper.

See what readers are saying about 101 Questions You Need to Ask in Your Twenties. 


  1. Kristi

    Great article. I think everyone can relate — me personally, #5 and #6 are things I deal with in my relationship. I will definitely be thinking about & answering these questions.

  2. Neil Bruinsma

    These are amazing questions! Thanks Paul!

  3. MJ

    STELLAR! I don’t know how I didn’t see this til today after a tweet from Love & Respect NOW!

    The questions about “vision for the future” is probably the one that hit me the most, from the perspective of my 20 years of marriage.

    Sadly, as you point out in many of your other posts, most 20-somethings (and 30 and 40) haven’t really analyzed their OWN vision for the future, much less are prepared to discern and scrutinize another’s.

    We’re trying to get wise individuals to do just that over in the Future Marriage University community where we’ll be sharing your spot-on advice: https://www.facebook.com/FMUniversity.

    Thanks again, Paul!

    • Tori

      I just wanted to say I SO needed to read this. THANK YOU PAUL excited to read more of your work.

      • Paul Angone - All Groan Up

        Tori, thank you for your comment. Looking forward to connecting more and being a resource.

  4. Almost 3 years

    I have been dating a guy for almost three years. Hes alost 29 and
    Has no known career goals, and never wants to talk about his future goals

    • Paul Angone - All Groan Up

      That’s a tough one! There might be some insecurities there that he doesn’t want anyone to get to close to.

  5. LA

    Great article! You made some really great points that I think are often overlooked in articles which strive to help you understand the health of a relationship. I sometimes get overwhelmed because I read these and want to be intentional, but how do I communicate it with my significant other? I don’t want to come off as though I have all the answers and put relationship “tips” in his face. He’s highly competent and a wonderful man but I get excited about this stuff and feel intentionality is important! Any thoughts on how to communicate with him without seeming forceful or manipulative, because that is not my intent at all! I just feel relational maintenance is important 🙂

    Thanks again for sharing!

  6. Jessica P

    Excellent article! This article helps anyone wanting to pursue a healthier and realistic relationship. Thanks for being so real, insightful, and honest.

  7. Susan Shain

    Awesome tips, Paul! I’m not dating anyone at the moment, so I’ll bookmark this for later!

    • josh

      i can fix that 😉

  8. Vicki

    Thank you so much for this article, this was something I really needed. I’m struggling to understand my own emotions in my current relationship and this article has really helped with that!

  9. Cassiti Allison

    Hey there!

    I absolutely LOVED this article. You really hit the nail on the head with so many of the problem areas that arise. Intentional communication and the understanding of how to discuss these things early on will allow many years of a healthier relationship.

    I did just have one comment though. As much as I completely agree with number 7, that your childhood family dynamics do play a role in your adult behaviors, I don’t think it stops there. I would have to say that it doesn’t necessarily mean that it will be the same. I’m a strong believer in resilience. When adults see where their childhood had some negative aspects, and they are growing and learning how to overcome those things, I think it’s a beautiful story. If the person you’re dating does have that not-so- ideal family, I think it’s important to have further discussions on that subject. (What they do and do not agree with from their childhood, which attitudes and qualities that they have received from each parent, how they have been overcoming the obstacles and making better choices for their own life, ect – there’s more of course)

    Coming out of a very unhealthy family myself, I have learned so much more about who I am and what my beliefs are on communication. I know exactly what I do not want for my future family and I have been taking active steps to make my future different than my past. It would be unfortunate for my dating partner to view my childhood as an indication for what my future will be like. I do understand that the family behaviors are a good thing to pay attention to in order to start having those discussions 🙂

    Thank you for the post!!! So helpful and I’ll definitely be sharing it with some of my friends.

    • Paul Angone - All Groan Up

      Awesome Cassiti and extremely well-said! Loved hearing your perspective and your wisdom. Definitely agree. If having a jacked up childhood precluded us from getting married or having healthy relationships, there wouldn’t be many marriages out there. Definitely sounds like you’re asking yourself the tough questions and being intentional about finding healing. So important. We all have monsters in the back of our closets. Definitely important to face them now so we can limit how wild they run that first year of marriage.

  10. Linda Franco

    Fantastic article!! Thank you.

  11. V

    I have a question. My girlfriend and I love each other very much but she does not like physical contact. She will not stand close to me let alone touch me and openly says she does not like contact. This is bad because I however love contact (such as a hug), I am in grade 8, what do I do?

  12. Belle

    Great article! Sharing with the our Young Adults group. 😀

  13. Guest

    Where are the real good old fashioned women that we once had many years ago? Today they’re everything, and not old fashioned at all unfortunately.


Submit a Comment

Your email address will not be published. Required fields are marked *

You’ve got questions.

We’ve got your-


SurVival PAckAge

A free, super-stuffed care package of resources to help you get through your twenties (and thirties too).

Order my new book "25 Lies Twentysomethings Need to Stop Believing"!

25 signs its a quarter life crisis

Instantly access: 

- "3 Ways to Pay Better Attention to the Answers Right in Front of You" - a quick, three step action guide to paying better attention that you can implement today.

- The first two chapters from best-selling author Paul Angone's new book Listen to Your Day: The Life-Changing Practice of Paying Attention.