I Dated Someone I Never Knew: Critical Questions to Ask Your Significant Other for a Better Future



Tackling everything from wellness, relationships, and everyday living, Katie Hagan uses her writing and experiences to inspire you to live a life that feels like coming home.

Tackling everything from wellness, relationships, and everyday living, Katie Hagan uses her writing and experiences to inspire you to live a life that feels like coming home.

Feet up on the dashboard, I gushed to my boyfriend about how I had it all figured out. After college, I was going to go into communications. I explained how it was the smartest way to make reliable money as a writer. By writing press releases, social media posts, and blogs for an organization, I was confident I could build a substantial income one day.

As the car crawled through campus, I knew he was idly distracted by the blooming trees and blossoming flowers. The one thing I did know for sure was that he deeply adored nature. Distant, he calmly said, “Money isn’t everything.”

If I was the one driving, I would’ve slammed on the brakes out of reaction. My first thought was to say, “Lord knows I’m not putting myself in this college debt for nothing, honey.” Rather than giving him an attitude though, I gently asked, “What’s that supposed to mean?”

“Money isn’t everything. I don’t really care about the money I make in life. I just want to be happy.”

As someone who was juggling three jobs, taking credit score workshops, and already thinking about the ways I could refinance student loans, I thought to myself, “After two years how did I miss? Has he never cared about money?”

Then, like something out of a That’s So Raven episode, all of these memories came flooding back to me. The camping trips instead of getting hotels and splitting meals together instead of getting two.

We weren’t doing that because we were in college; we were doing that because he genuinely enjoyed a simplified life. He sees no need to live lavishly, which is incredible, honorable, and downright shocking that it never dawned on me.

My hope for you is that you don’t let life distract you from knowing the details about your loved ones.

Curious and confused as ever, I continued to probe. I asked him to explain to me what he wanted his future to look like, and let me tell you, that opened Pandora’s box. I wanted the city, an exciting career, and financial security. He wanted to move back home to the town he grew up in, join his dad in the workforce, and live a worry-free life.

The way he talked about it was incredibly wholesome and remarkably sweet, very Hallmark-esque. To this day, it still makes my heart swell because it felt like it was the first time I ever saw him. It was in that moment that I had a gut-punching realization that we were headed in two wildly different directions.

Sometimes we avoid hard questions because we’re scared of the unknown.

By avoiding the inevitable, we’re depriving the people we love from fulfilling relationships. You can’t hog a human just because you love them at surface level. We all deserve a love that is thoroughly compatible. And it’s by digging into those hard questions that you find deep everlasting love.

Even if you think it’ll put you at a disadvantage, if you love the one you’re with, ask the hard questions.

The questions below, in no particular order, just begin to scratch the service. The answers will reveal characteristics, values, and important details about your significant other that may have been left out along the way (or avoided). Sure, some might seem so painstakingly obvious, but if you never straight out ask, how can you know for sure?

Before rallying them off demanding answers, start by planning for positivity. You should get excited to get to know more about the person you love. Opening a new dialogue might even make you fall a little bit harder.

Order in your favorite dishes before striking up the conversation. Maybe even write them on Jenga blocks, answering the questions as you choose the loosest link . Whatever you decide, ask these questions with an open mind and even more, an open heart.

  1. What kind of life do you imagine for yourself?

  2. On a scale of one to 10, how important is money to you?

  3. What kind of workload are you happy taking on?

  4. Do you like traveling? What’s your ideal vacation?

  5. Are you an animal lover? What are your thoughts on pets?

  6. What was your childhood like? What’s your favorite memory?

  7. What’s the most difficult thing you’ve been through?

  8. How do you cope? How do you celebrate?

  9. Is faith or religion important to you at all? Why or why not?

  10. What’s most important to you in life?

  11. What’s a deal breaker for you in a relationship?  

  12. Do you see yourself having a family one day?

  13. Who is your biggest idol and why?

  14. How much debt are you in? Do you have a plan to tackle it?

  15. Do you believe in life after death?

  16. What are your political views? Please be gentle through this.

  17. What’s your biggest pet peeve?

  18. Are you at risk for any serious diseases?

  19. Can you tell me everything you want me to know about you?

  20. Do you want to know my answers to these questions?