Executive Matchmaker Presents Great Questions To Ask Your New Love Interest.

After you meet a new person and while you are establishing the beginnings to date, you should get answers to these questions before you start dating. These important questions beg for an answer. They reveal a lot about what that person expects, and what that person is looking for in terms of their dreams, their spouse, their leisure time, and their ideals.

1. In an ideal relationship, what would you spend the majority of your time doing?

You need to be with someone who you would actually hang out with, someone who enjoys the same things as you. Yes, you can share each other’s different interests, but that’s why you need to ask this question, to see if you would enjoy adapting to their interests or if they would enjoy adapting to yours.

2. What do you expect from a guy/girl you’re dating? or What do you expect from a man/woman in your life?

You’d be surprised with the answers to this question. As humans, we assume that people have the same expectations that we do. Unfortunately, men and women are wired differently. That’s why this question is important. Not only are we different because of our genders, but we’re different because each person’s past experience helps mold their expectations and each person’s past experience is different.

3. What is your idea of living a good life?

Here you get a taste of what motivates the other person. You’ll get a taste of what drives them, what gives their life meaning and significance. It also gives you a view of what a future would look like with them.

4. What does a good relationship look like?

It’s always nice to know what the other person views as ideal in their eyes. You can see if you’re looking for the same thing in terms of what makes a relationship good.

5. What are you looking for in a guy/girl?

Let them name the top three qualities that are non-negotiable.

6. What have you learned from your past relationships?

Ideally, it would be nice to go through each of your past relationships, not to relive pain or point out the mistakes of your exes, but it’s important to know that the person you’re with has learned from their own mistakes and isn’t just moving forward ready to make the same repeat mistakes with you.


Give the person time to think about these questions. They need thought. Most of them can’t be answered right away. These are deep questions that could lead to lengthy conversations, but it’s important to know what you’re getting into.


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