As we wove through the dark valleys of the Pacific Northwest Cascade mountains, our headlights slicing a softly lit path for us on the freeway, I read another question. “Who do you believe your partner will help you become?”

Jared and I were driving back from our weekend in Idaho and left especially late to try and avoid Labor Day traffic. It was almost midnight. We’d rode in calm silence for several hours, but then I asked if we wanted to answer some premarital type questions. You know, things you’re supposed to talk about before getting married.

Our wedding is still months away, but it’s going to approach faster than a bug on a windshield. So we’re trying to be proactive. And this means answering the hard questions.

Questions about finances, having children, in-laws, finances and finances. When you choose to intertwine your life with someone, regardless of a marriage certificate, you need to start asking the hard questions both of the person you’re with and of yourself.

Years before, when I was dating a man who struggled with addiction-issues, I never asked him the hard questions. And, more importantly, I chose to not ask myself the hard questions either. When he was clearly going through an unhealthy patch and his behaviors were affecting me emotionally, I didn’t ask myself how I felt about it. I mean, I definitely knew how I felt. I was hurt, confused, anxious, scared, and insecure. But I still didn’t ASK myself what this meant for me and my own health. Because underlying the pain I felt layer of slight exhilaration. There is something about being near someone who is destroying their life that inadvertently makes you feel more alive.

I didn’t ask myself if it was what I wanted. If it was fair to me. If it was making my life healthier. I just drove, blindly in the darkness, steered by my emotions.

If you are trying to enter the dating world but struggle with shyness, nerves, insecurities, anxieties, etc etc etc, find strength in your ability to ask questions. Lead with an inquisitive mind. By inquiring into someone’s mind you are being bold and you are showing them you care about their thoughts.

Ask the person you’re with what they think makes a healthy relationship.
Ask yourself if you feel better or worse after you spend time with someone.
Ask the person you’re with what support looks like.
Ask yourself if you feel supported.

When you choose to spend time with another person, they are helping you become someone new. New, as in someone who has grown and matured. When you are dating someone, who are they helping you become?

Don’t be afraid to ask the hard questions. Critical thinking is like mental fertilizer helping your brain-garden grow apeshit hardcore.