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10 Questions to Ask When It Starts to Get Serious

When Justin and I first started dating, we asked each other a myriad of questions in an effort to really get to know each other. Some were serious. Some were funny. Some were simply asked out of curiosity.

Books or movies? Coffee or tea? Cook-in or eat-out? Quinoa or fries? Water ski or snow ski? Beach or mountains? Dogs or cats? Beer or wine? Extrovert or introvert? Night owl or morning person?

However, as we continued to date and continued to ask each other questions, they took on a different tone as we realized that our relationship was getting more serious. Suddenly, it didn’t really matter if he preferred movies over books, but it really did matter if he shared the same values and beliefs as me.

Here is a list of the top 10 questions (not in any special order) that we highlighted as the most important to discuss. The answers to these questions had the potential to be deal-breakers, and we wanted to be sure we were aligned (at best), and not blissfully ignorant (at worst).

1. How do you handle conflict or get things off your chest when you are upset? I wasn’t raised in, nor have I ever been in an environment, where people yell, hit or throw things when they are upset. I have been in an environment where people just shut down and avoid all conflict. Neither is healthy. We wanted to be sure that the proper balance existed when dealing with conflict so that both of us felt “heard.” Sometimes one of us will simply say, “you are bugging the crap out of me right now …” We may simply acknowledge that statement, or we may discuss it (depending on how serious it is), but we’ve found that’s a good balance for us between screaming and going silent!

2. Do you want any (or more) children? I was nervous that this was going to be a big question for us and one that generated significant discussion. We did discuss it a lot, but only because I wanted to be 100% sure that Justin would never second-guess his answer. You see, I already had two children, and he didn’t have any. Would he want to have his own biological children? He assured me from day one, and never wavered, that he would be perfectly fulfilled being the bonus dad (step-dad) to my children, and he has demonstrated this consistently over the past nine years. He was born to be their bonus dad and has embraced the role with his entire being.

3. What impact have your prior relationships had on you (any ‘bruises’ to know about)? We all come into relationships with chips on our shoulder (or baggage) from past experiences. There are just certain spots that remain tender and sensitive. When someone hits them, even unintentionally, it’s like hitting the nerve on a tooth. The pain flares and the response is instinctual. We talked significantly about where our sensitive spots were and how to avoid ever hitting those intentionally or unintentionally.

4. Do you practice any religion or have a strong faith? My faith is very important to me, and Justin’s faith was hugely important to him as well. We were fortunate to share the same faith, although we were both actively involved in two different churches. Our big faith decision came down to which church to attend as a family once we knew we were going to marry. I know we both would have had a difficult time engaging in a serious relationship with someone who didn’t have a faith at all. Being involved in our church together is a large part of our lives.

5. What is your perspective on money? I don’t believe in certain kinds of debt (like credit card debt or car loans) and fortunately, neither did he, but this can be a major point of contention between people. We quickly took a look at our stance on money and discussed things like how we were going to combine accounts moving forward. One of the best practices we implemented is a financial review where we sit down once a quarter with a glass of wine and take a look through our accounts simply to make sure we are both on the same page. It’s something we have done for years and has become a fun habit for us both.

6. What are your spending habits? Slightly different than the question above is a discussion about spending habits. Some people will only shop at Nordstroms and find it offensive to pay less than full price, while others, like me, enjoy the thrill of the hunt at a discount retailer like TJ Maxx. Fortunately for us, we both like nice things, and we both like to find a great deal. One of the things we agreed to early on is that we would simply let the other person know when we were spending beyond a certain amount on something (our threshold amount is $350). This isn’t an approval or a request, but rather simply a notice that one of us is making a big purchase in excess of that amount. It’s all part of keeping each other in the financial loop.

7. Do you tend to be the jealous type? I have never dated a highly jealous man, but I’ve watched friends date men whose jealousy came through strongly. I knew I didn’t want to be put into a position where I had to account for myself 24 hours a day. I want to be with someone who enjoys being with me, and wants to be with me, but not to the extent that I can’t go out with friends or do anything without him. I didn’t want to feel as if I was getting interviewed at the end of each business day about with whom I spoke or met. Thankfully he’s not the jealous type, nor am I, and that proved to be a short, but important, discussion.

8. What is your relationship like with your parents and/or siblings? If you watch how someone treats his/her family, it tends to provide great insight as to how he/she is going to treat you and your family. There is not necessarily a right or wrong answer here, but rather it’s a preference. For example, my observation is that Justin’s family talks almost daily even though they are all located in the same town. In contrast, my family is located across the country, and we talk about once a week. The common denominator is that no matter how much or little we talk about the daily, trivial things, we will all drop anything and everything if anyone finds themselves in crisis. That was an important criterion to us both.

9. How do you best feel loved? This is an important one since we all feel and show love differently. For example, I am not a gift person while others love to receive gifts. If you give me a gift, I will be appreciative but I won’t correlate that with love. If you help me out, however, with a project, or errands, or with something on my to-do list, I feel incredibly loved. The watch-out here is to be sure that you don’t assume everyone feels like and receives love the same way you do! Part of the challenge is to figure out each other’s love language (and if you haven’t done so already, read the book, The Five Love Languages).

10. What is your vision for our future? The answer to this question provides insight into what your partner is thinking … and whether that plan includes you. I am friends with a couple who recently asked each other this question. His vision for the future included retiring from work, moving to the lake, never getting on an airplane again, and golfing every day. Her vision included traveling the world with him and learning to cook authentic Italian food together (note, she doesn’t golf and never has). When Justin and I discussed this question, the right answer for me was more than him simply saying his vision was “being married to you for 30 years.” We could be married for 30 years and lead entirely separate lives. Rather, I wanted to hear his vision include something like, “I want to grow old with you, at your side, laughing, exploring, adventuring, traveling, spoiling our grandkids, …” It was important to hear that our vision was aligned and included each other. While I don’t want today to race past us, I do look forward to growing older together.

What do you think? What are other great questions to ask as you begin to get serious?


Monique Honaman 2013 HRLT2 265x180 Are You Dateable?About the Author:

Author Monique A. Honaman wrote “The High Road Has Less Traffic: honest advice on the path through love and divorce” (2010) in response to a need for a book that provided honest, real, and raw advice about how to survive and thrive through one of life’s toughest journeys, and “The High Road Has Less Traffic … and a better view” (2013) to provide perspectives on love, marriage, divorce and everything in between. The books are available on Learn more at