5 Questions to Ask When You Want to Know More

After the first few dates and even the first dozen conversations with an online match, you might think that you have already learned everything you could want to know about another person. The truth is that relationships are often a never-ending journey between two people who simply want to know each other more. If you are feeling stuck for new things to learn about a person aside from their hobbies, favorite things, and personal interests, try these questions on for size.

1. What Is Your Favorite Memory from High School?

Unless you were the star athlete, you probably don’t talk about high school that often. However, our school years are considered some of the best years of our lives. Asking this question helps you see what was important to your mate back then and how that memory has shaped who they are today. This question also gives both of you the chance to take a trip down memory lane and explore the differences in their upbringings.

2. Tell Me about Your Oldest Friend

The way we view our friends says a lot about us. Maintaining a friendship for decades is no small feat. By asking about your match’s oldest friend, you are making an effort to learn more about them and how their loyalty with this person has been tested over time. Chances are that they will have plenty of funny stories to share with you, and those stories will spur some of your own memories with your friends.

3. If You Could Do It Again, What Would You Change?

I often joke that I wish I could live my life a thousand times over so I could pursue so many other interests I have but do not have time for. This question is a great way to find out what other hobbies and interests your date has. We all have interests or careers that we would have liked to pursue but were not feasible with our situations. It is always fun to think about how such a change could have radically changed our lives.

4. Do You Have Any Superstitions?

Another interesting talking point is fears and superstitions. You can learn a lot about someone based on their beliefs in the supernatural or science – or both. Hearing the backstories behind superstitions is also interesting and gives insight into a person. For example, my family is Native American. Over the years, I have embraced my heritage more and more. I always have something with a turquoise stone on me because Natives believe that turquoise protects you. It sounds silly, but I feel a little superstitious about it! If someone asks, it gives me the chance to divulge what I do know about my heritage, which is quite interesting to many people.

5. What Is Your Best Memory with a Parent?

We can all think of a single memory with one or both of our parents that really stands out and makes us smile. This question helps you gauge the type of relationship and bond your partner has with their parent and also helps you see the types of memories that they think are important. It is often not the tangible things that make a memory but, instead, the moments where we felt the most love, happiness, and contentment.