Wondering how to find the one? Here are 5 questions to point you in the right direction.

5 Crucial Questions You Need To Ask When Dating

In Dating by Debra Fileta

Ever find yourself wondering how to find the one? Maybe you’re asking the wrong question. Check out this guest post by my friend, Paul Angone. You’re going to love what he has to say!


“How do I find The ONE?”

When I was dating I remember constantly chasing this one giant question.

The search felt like trying to magically stumble upon a chest of gold, at the end of a rainbow, that was being carried by a unicorn with leprechaun jockey.

Finding “The One” felt like a quest of mythical proportions that I was surely going to fail at. 

But then I changed the question.

Instead of asking how to find the one, I started asking “How do I know which “One’ is the right one? How do I know I’m becoming the right one as well?”

Instead of trying to lasso that magical unicorn before it flew away, I started asking better questions. 

And now 10 years and three kids into marriage, I still find myself asking these important questions about dating and marriage in different ways.

So if you’re dating someone, thinking of dating someone, or married and looking to continue deepening your relationship, here are five crucial questions you need to be asking you and your dating relationship.

5 Crucial Questions You Need to Ask When Dating

1. 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.

We act like 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.

Why don’t we talk more about the fact that attraction runs much deeper than looks?

Sure appearance might catch someone’s eye, but it’s personality, values, faith, heart, and your past, present, and future story that’s going to make you, and them, stay.

Your spouse is a gift. And attraction is the whole package. And what’s inside is much more important than the shiny wrapping paper.

2. Are we loving from our insecurities or are we loving each other from our strengths?

What’s the difference?

Loving from your insecurities demands from others. Loving from your strengths gives to them.

Loving from your insecurities does not want to see your partner succeed more than yourself. Loving from your strengths hears of their success and is the first to celebrate with them.

Loving from insecurities daily demands, “what are you going to do for me?” Loving from your strengths asks, “What can I do for you?”

If you “love” from your insecurities, your love will be more selfish than selfless. And honestly, “loving” from our insecurities can be the worst form of manipulation there is.

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.

Is their love based on YOU or is their love based on THEM?

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

Bonus Question: Have we tackled our 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.

3. Do I want to become more 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.

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.


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

4. How does my family communicate? How does my partner’s family communicate? And are my partner and I communicating about the crazy ways we’ve learned how to communicate crazily?

As I write in my new book 101 Questions You Need to Ask in Your Twenties:

We all go through intense communication training for years; it’s called childhood.

It only takes one Thanksgiving dinner of intentionally listening and studying your family to realize that the cranberry cheese log on the table makes more sense sometimes than your family does.

And it’s hard to unwire eighteen 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. And this does not mean that if your family didn’t exactly model healthy communication that you’ll never have healthy relationships. If having a di cult childhood precluded us from getting married or having healthy relationships, there would be about thirteen marriages out there.

However, it is good for all of us to realize that 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 on how to communicate. 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 this test will come like a train on a dark and stormy night when your car runs out of gas on the tracks! I promise.

5. Do our soul values and beliefs repel or compel each other?

I believe one of the greatest causes for conflict in marriage are what I call contradicting soul values.

I’d describe soulvalues 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 write in my new book 101 Questions You Need to Ask in Your Twenties: (and let’s be honest, your thirties too)

“If your soul values can’t dance together, then you’ll keep tripping, falling and wondering why you can’t move together in rhythm.” 

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 of risk-taking, as she enjoys change and pursuing things off the beaten path.

What are your soul values? Can you write out your top five and rank them from most important to least? Can your partner do the same? Compare notes and plan accordingly.

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

This post is adapted from Paul Angone’s just-released new book 101 Questions You Need to Ask in Your Twenties: (And let’s be Honest Your Thirties Too) Dive deeper into 96 more important questions you need to be asking about your relationships, career, and life purpose in this incredible and insightful new book