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Dating

Questions to Ask on A First Date: According to a Matchmaker

First dates can be a mix of excitement and nerves, but asking the right questions can make all the difference in fostering a meaningful connection. As a matchmaker, I’ve seen firsthand how powerful a great conversation can be in building rapport and uncovering compatibility. Here are my top six questions to ask on a first date to spark engaging conversations and potentially lay the foundation for a serious romantic connection.

1. What’s something you’re really passionate about?

This open-ended question encourages your date to share what they love most. It’s a wonderful way to learn about their interests and what makes them tick. Plus, seeing someone light up when they talk about their passions is always a joy and can be quite infectious.

2. What’s the most interesting place you’ve ever visited or want to visit?

Travel stories are a fantastic way to bond. This question can lead to exciting tales and shared experiences. Whether it’s a local gem, an exotic destination, or a dream trip they haven’t taken yet, you’ll get a glimpse into their sense of adventure and curiosity, and maybe even find some travel inspiration of your own.

3. What do you enjoy doing in your free time?

Understanding how your date likes to spend their downtime gives you insight into their lifestyle and hobbies. It’s a great way to find common interests and potential activities you might enjoy together. Sharing these interests can also open up more relaxed and natural conversation flows.

4. What’s the best piece of advice you’ve ever received?

This question can reveal a lot about your date’s values and experiences. It often leads to deeper conversations about life lessons and personal growth, helping you connect on a more profound level. It’s a window into their mindset and what they hold dear in life.

5. If you could have dinner with any person, living or dead, who would it be and why?

This fun and imaginative question can lead to fascinating discussions about your date’s inspirations, heroes, and interests. It’s a great way to understand more about their personality and what they value in others. Plus, it often brings out interesting stories and dreams.

6. What’s one thing you’ve always wanted to learn or try?

This question taps into your date’s aspirations and dreams. It can lead to engaging conversations about future goals and interests that you might both share or find intriguing. It’s a great way to discuss ambitions and see where your paths might align.

Remember, the key to a great first date is to foster a two-way conversation. Pose open-ended questions and encourage your date to share more about themselves. For more inspiration, check out the 36 questions listed by The New York Times, designed to spark deeper connections.

By asking these questions, you’ll not only make your date feel valued and heard but also create an opportunity to form a genuine connection. Keep things light, show genuine interest, and most importantly, have fun! Happy dating!