Dating for everyone is going to be different, and can move on different timelines. No matter how that looks, there are questions you should ask your dates to gather information for compatibility purposes. Plus, dating can be awkward at times, and this will give you icebreakers and open doors for additional conversations.

“What Are You Looking For?”

In today’s dating world, you can never know what someone is looking for. It’s not safe to assume everyone is looking for something long-term. You want to make sure your date is on the same page as you before you get too deep into anything to avoid wasting your or their time. Find out if they want something serious or just keep it casual. Are they going to be exclusive? Are children on the radar for the future? All important things to know from the get-go.

“How Would You Describe Your Family & Friends?”

You can tell a lot about someone based on who they surround themself with and what their relationships look like. Are they a tight-knit group? Do they interact frequently? If so, family and friends are probably a top priority for them. See how they view those people who are close to them and what they say about them. It will also give you some insight into what they are looking for in a partner. Can you see yourself fitting in with their group?

“What Are You Most Proud Of In Your Life?”

This question can be very informative and possibly entertaining. First of all, how do they react? Maybe they will feel shy and a little reserved. Or they can give you a dissertation on their accomplishments. It allows you to see how they view themselves and how deep they will get with you. It also can show you what types of things they value. Their response can be superficial, or it can be something of significance. You may even get a great story that opens the door for some quality conversation.

“What Are Your Goals?”

Knowing what someone wants in life and what they are trying to achieve can shed some light on their future. You most likely know your own goals for the next year, five years, and long-term. How do their goals match up with yours? If you two have very different ideas for the future, your stars may not align. Also, if you have competing goals, there is an opportunity for conflict in the relationship and something you would have to plan for.

“If Money Was No Object, Where Would You Live & What Would You Do?”

If money wasn’t an issue, where would they want to be? Are they a city person or a country person? Would they want to be somewhere obscure, international, or close to their loved ones? It can also tell you what they would dream of doing. Would they continue to work some type of job or treat life as an adventure? See how their answers line up with your own. While it is a hypothetical situation, it tells a lot about how a person would live their life if any circumstances could change. Anything is possible, so make sure you’re on similar pages.

“What Are Your Political Views?”

This may have been more taboo years and years ago, but in today’s world, where politics is so intertwined with many factors in life, it could be helpful to know where they stand. First of all, do politics matter to your date, and with what significance? If you both value politics on some level, you should also know where you both fall on the spectrum to avoid future conflict. Maybe it can be healthy table talk to challenge each other. Or maybe the difference in viewpoints is something you can’t get past. Either way, it is helpful to understand early on.

Being able to be open and honest in the beginning is important to a lasting relationship. Mix in fun and light questions with serious ones. If you’re finding it difficult to navigate your dating journey, relationship counseling can help. Contact me and let’s talk about it.