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10 First Date Questions

First dates can be tricky and a bit awkward. Until you know one another well, it’s really hard to let conversation flow. Here are a few questions to help you out of what can be a sticky, awkward situation.

1. Highs and lows: Many people know the old “tell me something good about your day” trick, but mix it up! Ask about the highs and the lows of their day. Both are equally telling, and can easily provide fodder for other conversations.

2. Favourite movie of all time and why: By tacking the “why” on, you get a little glimpse of what they’re into. Love story? Car chase? A drama with awesome characters? Non-stop laugher? Get inside their head a little bit. Better yet, remember this detail and rent the film later OR see a similar movie in the theatre.

3. Tell me one thing about yourself that would surprise people. It’s easy to assume we know someone based on what they look like or how they behave. By asking someone what others would never expect, it’s a good way to get a sense of a hobby you might also enjoy, and a detail you might not have known from their online profile or initial introduction.

4. How long have you known your oldest friend? What makes the friendship special? You can learn a lot about someone by learning about the people they surround themselves with and how they relate to them. Also, it’s a good potential red flag spotter: if someone has no close friends to speak of, that’s usually kind of a weird sign. Just something to keep in mind!

5. What does your ideal weekend look like? Learning how someone loves to spend their free time is great for planning future dates and also getting insight into what that person enjoys. Be sure to note the activities they’re into for future plans.

6. If you had to read one book for the rest of your life, what would it be? Reading habits are really revealing. Do they choose a love story? An adventure? A self help book or religious text? If you’ve never read the book, ask them for a synopsis and go from there.

7. Name someone you admire. Why do you admire them? I love learning about fascinating people and I also love hearing why people I am talking to admire the people they do. It can sound a bit like a job interview question, so phrase it well, but if you play your cards right, it’s a great intro to learning important things about your date!

8. What’s the best meal you’ve ever had, not just in terms of food, but also experience? Most people have a few noteworthy meals in their life, not food-wise, but the experience. This question gives you a ton of insight: do they enjoy a lot of noise around a crowded table, or is a romantic, quiet dinner more their scene?

9. What’s the scariest thing you’ve ever done? Most people have tried to overcome their fears and love sharing times when they were successful. Talking about what you’re afraid of is also a great way to get a little vulnerable.

10. Tell me about the best part of your job. Most people consider their career a huge part of their life. Learning about the best parts and what makes them “tick” is an awesome way to get to know part of a major part of their life.

What’s the best or worst question you’ve ever been asked on a date?

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