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First dates are notoriously awkward. Even if you’ve been around the person before, the expectations and pressure of an official date can still cause anxiety. The first step is to choose an activity that allows for conversation so you can get to know each other better. But what if you don’t know what to talk about besides something mundane like the weather or charged like politics? Try these five questions to encourage meaningful conversation.

1. What are you reading right now?

This question usually reveals your date’s interests. You can tell a lot about a woman by the books and genres she reads. It’s also a fun topic and can shed light on common interests. This usually is a safe subject as well, though it can lead to trouble if the book is about something controversial. If that’s the case, just move on to another question.

Maybe your date isn’t a reader. That’s okay. The question can open up conversation about other forms of media and entertainment instead.

2. How do you like to express yourself?

This is a more personal way to ask a woman what she likes to do. Instead of rattling off a list of hobbies, she has to think and choose the ones she uses to express herself. They could include:

• Art
• Music
• Writing
• Blogging and/or social media
• Fashion
• Dance
• Crafts
• Service and activism
• Physical activity
• Cooking
• Work

You’ll probably also learn the backstory of how the activity became an important form of personal expression for her.

3. What is the most exciting or meaningful place you’ve traveled to?

Asking about an exciting travel destination lets you know the cultural and geographical tastes of your date. You can see if she has a sense of adventure or wonder and discover how globally experienced she is. Asking about a meaningful location reveals the people, places, and memories that are central to her. It can also evoke emotion, which will help you two connect more than you would had you only engaged in small talk.

4. Who has been the biggest influence in your life?

Other variations of this question are “Who is someone you admire?” and “Who is someone important or influential you would love to have dinner with?” Although similar, they each can get a different response. Either way, you’ll learn what kind of person your date appreciates, respects, values, or emulates, which in turn will tell you what kind of person she is or wants to be.

5. What was the best day of your life?

The answer to this question may be something unsurprising, such as a reaching a certain milestone or achievement, or something unique and less outwardly grand, such as a memorable day with a loved one. It will show you the people, memories, and events that hold the most significance to your date. The question can ease your date’s nerves, too, as women tend to get excited and talkative about people and times that are special to them.

Asking these questions on your next first date will enable you two to relax, open up, and get an idea of who you each really are. The resulting connection will also increase the chances of there being a second date, and you’ll have plenty of helpful information for planning a successful one.

Tags: conversation, date questions, first date questions, questions