Share Your Thoughts

Q I don’t have a lot of dating experience, and find it difficult to keep the conversation flowing on first dates. Any suggestions?

A You aren’t alone—keeping first date conversation flowing can be difficult for many. Here are five questions to ask your date in order to keep the conversation flowing.

What’s Your Favorite Thing About Yourself?
It can be difficult for many people to talk about themselves, especially in a positive light. This question not only causes your date to think about their good qualities, but it will also show them that you want to learn more about them. The answer can also tell you a lot about your date’s character and what they value in life, as well as give you ideas for what you should talk about.

What Motivates You in Life?
Motivation is a key factor that keeps us all going. Understanding what lies behind what an individual does can reveal information regarding what is important to them and what they hope to accomplish in the future. The answer to this question can reveal details without making the other person feel scrutinized.

What’s Your Favorite Place?
This question has no wrong answer and allows your date to share a special place. It could be a favorite vacation place or someplace important because of a past experience. Most people are eager to talk about where they love to spend time.

What Do You Do for Fun?
If your first date is going well, you will need to come up with some great ideas for your next date. Asking this question can spark new ideas and help you plan for the future.

What Do You Hate About Dating?
It may seem silly to ask someone why he or she hates dating, but the truth is that most people dislike at least one part of the process. Understanding what drives the other person crazy about dating can help you avoid it and increase your chances of success.

Learning about the other person is one of the most important aspects of a first date. Asking these questions can help you achieve that goal.

Jasbina is the founder and president of Intersections Match, the only personalized matchmaking and dating coaching firm serving singles of South Asian descent in the United States. She is also the host of Intersections Talk Radio.

Jasbina Ahluwalia

Jasbina Ahluwalia adds a unique contribution to the Matchmaking industry–she has pioneered an approach to matchmaking, which blends the best of the East and the West. She is an Indian-American attorney-turned-entrepreneur,...