If you have taken the big leap of dating again after a change in life circumstances, you have a million questions. Many are about the process of dating: whether to go online, pondering what dates will be like, wondering how you will feel on a date…and more. These concerns are totally normal and natural.

In my work as a relationship coach, women also ask how they can fast track getting to know the people they date. This need takes on particular urgency with meeting men on dating apps. Without the benefit of having background information from shared circles — typical in getting to know someone the “old fashioned way” — online dating feels a bit like having blinders on.

What’s the workaround? To accept that the responsibility for discovery falls squarely on you. It is to your benefit to figure out as much as feasible about the men you’ll go out with. Why should you care? Because gaining context about the history, values, attitudes, behaviors, preferences, and personalities of those you date will reveal who they are, AND predict whether dating them is worth your time.

The #1 Best Way to Get to Know Another Person

Short of having years to observe the person you are dating in all kinds of situations and under all types of pressure, what is the definitive way to know another person? Ask questions, and lots of them!

When I was a child, I was often embarrassed by my Southern mother’s style of asking questions of people she didn’t know. Back then it seemed awkward. Fast forward to adulthood, and I adopted her technique as a primer for building connection. I have employed it ever since.

Five Tips for Asking Great Questions

Here are five ways to know if you are on the right track:

• Does the question feel genuine? Think of how you’ll feel asking. If the premise makes you uncomfortable—or you wouldn’t want to answer the question yourself – skip it. For example: “What’s your idea of a perfect weekend?” seems contrived. It suggests you might want to spend the weekend, when perhaps you don’t. And a speculative answer hastily pulled out of a hat may offer nothing of value. 

• Will the question put the listener on the spot? If you have a concern the question violates privacy boundaries or requires too much of a revelation too soon, skip it. Examples are questions about failed relationships, life disappointments, or commitment preferences. Don’t ask: “Do you want to get married?” unless you are prepared for the answer! 

• Does the question show an authentic interest in learning more? Asking good questions is rooted in wanting to deepen a relationship as opposed to conducting an inquisition. It’s about caring to hear the answer instead of listening to yourself talk. A good example of a question which opens the door to learning more is: “What drives you to do what you do?” 

• Does the question build on the conversation? Yes, you’ll occasionally ask questions which prompt short answers. But to advance the discussion, think about ways to avoid monosyllabic responses. One of my favorites is the question: “What causes do you feel strongly about?” 

• Is the question playful? To ascertain if your date has a sense of humor, be lighthearted with some of the questions you ask. I always want to know the answer to the question: “If you could have any superpower, what would it be?”

How Curious is It Okay to Be?

Be as curious as the relationship will support. The game of building blocks is a metaphor for how strong the foundation of a relationship needs to be to absorb ever more interesting questions.

• Layer #1: establishing rapport. Finding common ground, comparing likes and dislikes, and enjoying each other’s company happens at this level. You have to get along before moving to more personal topics.
• Layer #2: sharing history. Understanding backgrounds, family, friends, and work history is discovered at this level. Having this information is key to knowing who the person is.
• Layer #3: identifying future plans. Learning about goals and personal growth is the most importantly intimate stage, and reveals where the individual sees themselves beyond today.

You won’t be sorry that you took the initiative to get to know the men you date. Devise your own questions for each dating situation you encounter. But always have a plan for asking – and listening and learning – to discover the merits of those you date.

Good luck and happy conversations! Share your great questions at Kate@KateSomerset.com.