10 First Date Questions You Can Ask to Ensure the Conversation Flows

Thomas Edwards
First Date Questions
When I speak with clients about first dates, the number one question I get is how to prevent the conversation from becoming an interview. On dates, there’s a tendency to ask questions that either result in “yes” or “no” responses or have little to no substance to dive deeper.

While some advice out there says to not have a list of questions, I believe you can ask all the questions you want on a first date, as long as you ask the right ones.

It may seem odd to have a list of questions you want to cover on a first date, we recognize that.  While we want to encourage you to let the conversation flow between the two of you, we think it’s always nice to have some “go-to” questions in your back pocket if the conversation starts to stall.

So to avoid asking questions that lead the conversation into a tail-spin of awkward silence, here are 10 questions you can ask that will have the conversation going all night.

  1. What is your biggest pet peeve? 
  2. What’s the next place on your travel wishlist?
  3. What are the 3 movies you need in your library if you’re stranded on an island?
  4. What’s your guiltiest pleasure?
  5. What’s your star sign? 
  6. What’s your go-to karaoke song?
  7. What are you most excited about in your life right now?
  8. If you had the day off tomorrow, what would you do?
  9. What’s the one thing in your life you’d like to share with your partner?
  10. If your humor was a comedian, who would it be?

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Question #1: What is your biggest pet peeve? 

People get really impassioned on this topic, no matter how ridiculous it may sound. There’s an opportunity to see if that pet peeve aligns with yours, allowing you to laugh about it and share an intimate moment.

Question #2: What’s the next place on your travel wishlist?

People love to bond over places they’ve been or desire to go to. This will also tell you about your date’s personality and whether their sense of adventure matches up with yours. Do they like to chill by the beach or are they a sightsee-around-the-city type?

Next Travel Destination

Question #3: What are the 3 movies you need in your library if you’re stranded on an island?

Movies are a great way to see inside what they enjoy watching in their downtime. If you want, you can even make them choose the best in each genre –– Comedy, Romance, Action, etc.

Question #4: What’s your guiltiest pleasure?

There’s an opportunity for a bit of playful teasing here. But if you do, make sure to then respond with your own equally embarrassing guilty pleasure. 

Question #5: What’s your star sign? 

This question is interesting because, first you find out if they’re into astrology, but you also see what qualities they identify with aka which qualities they think they possess.  It’s a much better way of asking the “what are your best (and worst) qualities” question in a fun way. Plus, you get better, more honest responses out of them. They end up being the things they feel they identify with.

Question #6: What’s your go-to karaoke song?

This is a fun question and potentially your next date idea happening at the same time. This gives you an idea of what kind of activities and the type of music they enjoy. This type of question can also easily lead to revealing and sharing Spotify playlists with each other.

Question #7: What are you most excited about in your life right now?

There’s no better way to see someone light up than when they’re talking about what they’re excited about? Here, you can let them go on and on, while feeding off their excitement with curiosity and wonder. This also allows you to see what’s important in their life should you be a part of it.

Question #8: If you had the day off tomorrow, what would you do?

Spontaneity provides one of the biggest joys in life and, if that’s important to you, you get to see if your partner shares that mentality. Whether it’s staying in bed all day or going on a daytrip, this will open up you and your date’s imagination, seeing whether those plans align with what you’d do.

Day Off Spent in Bed

Question #9: What’s the one thing in your life you’d like to share with your partner?

While we all desire a relationship and connection with a partner, it’s the little things that mean the most when it comes to what that looks like. Seeing what your date looks forward to sharing and airing your goals on that front is a good way to see if you’re a good match. Whether this is a love or art or a desire to learn more about international cuisines, you might find your potential partner’s goals to be perfectly aligned with what you’d like to share.  

Question #10: If your humor was a comedian, who would it be?

Sharing laughs and having humor is vitally important to relieving anxiety and stress during a first date — and this is a valuable tool to have even when you are deep into a relationship. Whether you two share the same sense of humor or not, it’s just as important to know what style of communication they use and when.

Have Your Own Answers Ready as Well

While these questions are amazing conversation starters, be prepared to respond to them yourself as well, since the intrigue will lead your date to want to know your answers, too. And while these questions provide more than enough guidelines, feel free to add your own style so it feels as genuine and authentic as possible.

As you can see, these questions open up the possibilities of where the conversation can go. You can even revisit a previous question once one conversation ends. When the conversation feels natural, you’ll come off as genuinely and refreshingly inquisitive without it feeling prescriptive. Do it right, and your date will be impressed with how easily conversation flows between the two of you, ultimately creating more attraction and connection. 

Making the conversation fun and dynamic will send your chances of getting a second go through the roof!

Thomas Edwards
Thomas Edwards founded The Professional Wingman to help singles find long-term relationships by developing their social skills through experiential coaching. With his first-ever publicly available course, Dynamic Dating, Thomas teaches you how to create a lifestyle conducive to meeting, attracting, and getting into a relationship with women both online and offline, while staying true to who you are.