Top conversation initiators to use on a first date

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First dates can be full of surprises and unexpected moments. While there’s no such thing as a cookie cutter formula to the perfect first date, there are questions that can tip things in your favor. There’s something really attractive about a date asking well thought out questions that keeps you engaged and interested.  Below are some of the best used questions that focus on learning more about your date’s personality, compatibility and gauge of connection. Remember to keep it conversational. The questions below should come out naturally, and really be based on what you may already know about your date, or want learn about during the date. This way you minimize that awkward silent moment that kills any shot of a promising first date. Use these conversation initiators and see where the conversation takes you. Leave a little room for the unexpected, pay attention to their responses and body language when you ask the questions.

Conversation initiators

  1. What’s a typical day like for you?

This is great question to learn more about your date. It’s much more personal than the old “So what do you do for work?” question. The response gives you a bird’s eye view about their careers and what they spend their free time on.  This can lead to follow up question such as, “how long have you been doing that?” which can be interpreted as how long they’ve been working on a specific job or career, as well as hobbies or passions that take up their time.

  1. What’s it like to do (name one thing that your date mentioned when talking about their typical day)

This is nice follow up to show interest in the conversation, and show that you’re paying attention to them. It’s also a good way to get them to open up more by saying back what stood out to you, which can make your date feel good about your interest towards them. This works really well when you follow your own curiosity about the topics that your date is telling you. Once you’ve felt that they’ve described it a bit, you can follow up with question like “that sounds amazing I’d like to know more about it?” it also puts out the impression that your attentive. It’s a sexy trait to have, and counts towards extra brownie points to a potential second date.

  1. What sort of vacations do you like to take?

This is a good lead question to get your date to open up about the details regarding their getaway destination spot, and activities that interest them. You can also follow up with questions like “what’s your favorite thing about that vacation? Take the time to gauge your date’s level of interest. If it’s starting to look like you’re beginning to get them to open up, feel free to start asking more interesting questions to really get to know the other person.

If you get stuck, here is our master list of first date questions.

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