5 Ways to get to know your boyfriend or girlfriend better

“Heading down south to the land of the pines
I'm thumbing my way into North Caroline
Staring up the road and pray to God I see headlights….
Rock me Mama. like a wagon wheel, Hey Mama rock me…”

As the firelight flickered on a beautiful evening in Italy, everyone in the circle bellowed out the refrain to “Wagon Wheel.” Catchy and easy-to-learn, this song was a favorite for our firepit evenings on the patio of the villa we stayed at in a little hilltop town. Little did I know that the leader of those fireside sing-a-longs would eventually be my boyfriend, and then husband, a few years down the road.

Even more surprising to me, if I had known, would be that watching him lead those sing-a-longs was a very important window into who he was — and would be more helpful in deciding if I wanted to spend a lifetime with him than many of the dates and conversations we would have while dating,

Dating can be a confusing and frustrating endeavor in today’s world -- especially if you are looking for marriage in the long run (and not just a short or long-term relationship). Looking back, many of the special, intentional dates I went on were less helpful for discernment than I thought. Instead, observing how my acquaintance (then friend, boyfriend etc.) interacted with others in various scenarios was key for figuring out if this was someone I could say yes to for marriage.

I’ve thought of different situations that shone a light into my husband’s character and personality, and I asked him to share the times he saw me in a different way that helped him discern. Together, based on those reflections, we created these date ideas that will hopefully give others an approximate way to better understand who a person is.

Just be aware this shouldn’t be seen as a pass/fail test for the person you are dating, but as a sincere attempt to come to know and understand each other – and as a practical way to help you each figure out if you would be compatible as a married couple.

One of our favorite dates was when we volunteered at a homeless shelter together. It was many hours, a half day event, and I got to see him use his strengths in his interactions with the fellow volunteers and the people we met and served. I also got to see him stretch out of his comfort zone and saw how he navigated the challenges that came up.

Does the other person follow the instructions carefully, or just enthusiastically jump in and start fitting pieces together? Can you work as a team easily? How do each of you deal with frustrations that come up? 

Your church might have a small discussion group, your local library might host a talk followed by a discussion, or a local establishment might have a weekly craft night, etc. For both of us, observing how the other interacted with a group of strangers or passing acquaintances in a more intimate but casual setting taught us a lot about each other.

Planning and executing an event, be it just a small, casual brunch or a more involved dinner party, is a great learning experience and peek into how someone operates.

How do you each interact with kids? How do you work together while serving other people in this way?

If your boyfriend or girlfriend is comfortable with the idea, you could visit them at their workplace or attend a work event together. If there is a way to see someone at work, and in their work environment (especially if they enjoy their job), find a way to make that happen.

Try to spend time in each other’s favorite places or with each other’s favorite people. Where does the person who you know and love feel most comfortable and alive? For some, this might be a childhood home, or a specific park, restaurant or place. For others, this might just be spending time with a beloved sibling, grandparent, or long-time friend.

Discovering what and who makes someone come alive requires more than just a cursory knowledge of the other person but is such a helpful piece of discernment. When you see someone in a place that is meaningful to them, or hanging around with a person they love, you get to see them alive in a way that can’t be replicated.

All of these dates and experiences will provide windows into who you each of you are. Sometimes, those windows will show your defects and flaws, as well as the baggage you’ve picked up along the way. However, the point is not that these dates will show you in the best possible light. Instead, the key is that you, the real warts-and-all-you, will become visible. Then, when it is time to ask the question, “Is this person someone I can spend the rest of my life with?” it should be easier to give your wholehearted yes or confident no.