Helpful Questions to Ask Before You Get Into a Committed Romantic Relationship

Is there a reason why you are hesitating?

Christy Janssens
7 min readFeb 23, 2021
Photo by Joanna Nix-Walkup on Unsplash

My boyfriend and I knew each other for five years before we started dating. It was one of those relationships that slowly evolved from acquaintance to friend to that weird in-between space where friendship seems like the wrong word to describe your relationship but you aren’t actually dating yet.

We are both commitment-cautious people, so the decision to date came after a lot (a lot, a lot) of conversations. We weighed the pros and cons and did some soul searching. We finally did decide to commit and we’ve been together for a little over four years now.

I remember feeling confused about how people actually decided to take the leap with someone, romantically. I’m sure it is a different process for everyone and that is okay. If you, however, are an over-thinker like me and would like some practical questions to help you determine whether this person is worth committing to, here is a list of what I asked myself while weighing this decision.

Please note that I am not a therapist or a relationship expert. These questions were born out of experience and what I found helpful in the decision-making phase.

1. Do we share similar fundamental values?

Do you share similar views on things like having children (or not), anti-racism, faith, work ethic and make-or-break subjects along those lines?

You have to distill your own core values and non-negotiable beliefs first. This doesn’t mean that you will never change or evolve as a person, but you have to have a foundation of what is important to you in life. Then you can hold it up to your person’s beliefs and values and have a real, honest conversation with yourself.

Some things might have a little room for different opinions but if there is a fundamental mismatch between your strongly held values and beliefs, that is going to cause conflict and possibly resentment in the long term.

2. Do I feel like myself when I am with this person?

Can you relax, be stupid, be honest with this person? Do they embrace your humanity?

If you feel as though you are changing or hiding true parts of yourself when you are around this person, that is a red flag.

3. Does this person bring joy into my life?

Sometimes we are attracted to certain elements of a person but something still feels missing. Maybe they are very smart or good-looking or extremely nice — or maybe all three! All of these qualities are amazing but nothing beats a person that brings genuine joy into your life.

Can you laugh with this person? Do you feel excited to see each other? Do you feel at home with them? Are they a bright spot in your life? If not, you might not have enough of a spark to carry your relationship through the long haul.

4. What is their style of communication and what is mine?

Are they blunt? Do they like to debate? Are they external processors or internal processors? Do they tend to avoid talking about their feelings?

I don’t think there is one communication style that is an automatic deal-breaker unless there is a pattern of terrible communication that you cannot get over. If you absolutely can’t handle the way your person communicates (or doesn’t) this is going to spiral out and create more problems in the long run.

If you are having issues communicating but you can talk about it with your partner and make a plan to get better, this can probably work.

This was what happened in our relationship. I was so scared, at first, that bringing up anything negative would cause a fight or cause a breakup. I didn’t talk about anything that bothered me and expected my boyfriend to read my mind all the time. This pent up a lot of resentment and frustration on my part that eventually exploded.

I also had to learn that my boyfriend likes to debate. Debating topics is like a conversation to him. I learned that he wasn’t arguing with me when he played devil’s advocate or presented an opposing opinion to what I said. It was simply his way of feeling close to me in that conversation.

We had many talks over the years about what we need from the other person in terms of communication. It took some work but, over time, our communication improved and our relationship is much stronger for it.

5. What is my long-term vision of where this relationship will go? What is theirs?

Do they line up in a way that is satisfying for both of you?

6. How do they handle their finances?

Look at the differences and similarities in the way you both approach money. Are you okay with the way they handle their money? Would you be okay with that long-term?

If one person is a spender and the other person is a saver, that might cause some tension in the relationship. It is important to explore where your money behaviour comes from. How was money treated for both of you growing up? What did your parents or guardians teach you about money? What are your partner’s money expectations for the future?

If you are not on the same page, this warrants some clear conversations about expectations and potential compromises that both of you are comfortable with. If this is an insurmountable challenge, you have to expect that it isn’t going to get better once you commit to the person.

7. Does this person encourage me to be the best version of myself?

Do they genuinely want you to develop my passions and dreams and sense of self? Are they willing to grow alongside you? Do they allow you to pursue what makes you thrive?

One small example of this: my boyfriend is an extrovert and I am an introvert. My boyfriend needs social interaction, stimulating environments, and newness every day to be his best, healthiest self. I need quiet space, time alone, and steadiness to be my best, healthiest self.

In order for our relationship to work, we had to be comfortable with giving each other space to be our best selves separate from each other. I am totally happy with him developing a social life and having experiences without me because I can’t possibly keep up with all that stimulation. He doesn’t expect me to do everything with him, either, because he knows I need space and time alone.

When we give each other space to be our best selves, we function better as a partnership. We don’t expect to like all the same things or do everything the same way. We plan to do some things together and we make sure the other person feels free enough to pursue what they need to thrive.

Another example: my boyfriend is totally uninterested in writing. However, he is the biggest cheerleader when it comes to my writing. He’ll find obscure writing competitions for me to enter and he’ll brag about my writing to anyone who will listen. That’s the kind of person you want on your team.

If you or your partner is unwilling to let you be the best version of yourself, then the relationship is going to turn toxic fast.

8. Is there any reason I am hesitating to commit?

What is it and why?

If everything seems good on the surface, but you are still hesitating to commit, have an honest conversation with yourself. Are you feeling insecure in some way? Are you getting a bad feeling about something you haven’t had the confidence to name yet? Is something in your past blocking you from saying yes?

There are so many different reasons why hesitation might arise in the face of commitment. You have to dig into what your reason is and understand why it is coming up. The answer might not be an intellectual thing, by the way. You might have to listen to your gut.

9. How does this person take constructive criticism?

If a person is consistently defensive or unwilling to listen to feedback, this signals a recurrent, unhealthy pattern. This is going to block your ability to communicate honestly and comfortably in the relationship.

I’m not talking about their reactions to straight-up, harsh criticism. I’m talking about recognizing areas of weakness in themselves and being willing to make changes for the better.

If a person is unwilling to change their mind or their behaviour when it is hurtful or unhealthy, then that is a problem. You are consistently going to be tempted to compromise yourself to make them feel better and that is not going to be good for the relationship. Shut it down.

10. How does this person function in a partnership?

Ultimately, you are picking a teammate. What kind of teammate do you want?

If you can’t see this person working well in a partnership, you might want to consider not committing. If you really think this person is great and you still want to try it, you have to have an honest conversation about your concerns first.

Final thoughts

This list of questions is not exhaustive but it is a solid start. If you breeze through these questions and there are no major red flags, this relationship is probably worth exploring in a deeper way.

Of course, not every relationship works out even if it is good. Please don’t feel as though you wasted your time if this is the case for you. Every relationship is going to give you more knowledge about yourself and what you may or may not prioritize in the next partner you choose (if that is what you want).

Nothing is wasted.

Know that all relationships, even the healthy ones, hit some rough spots but if you pick a quality person as a partner, those rough spots have the potential to bring you closer and deepen your intimacy. That is priceless.

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