Awkward silence is the killer of promising first dates. Fortunately, we’ve researched 13 great first-date questions to ensure you never have to endure that painful silence! The only thing worse is bad small talk. I want to help you banish both from your dates.
According to research, a flexible communication style—engaging questions, open-mindedness and easy back and forth is most effective.
Below, I outline my favorite first-(or second-, third-, or fourth-) date questions and conversation starters. Here is what they will do for you:
- help you to gauge more quickly if you have a connection
- get to know their personality, history and areas of compatibility more quickly
- encourage great conversation
Special Note: These are not meant to be pelted at your date in an interrogating manner. They should come up naturally, and (hopefully) lead you on delicious conversational tangents so you can forget the questions entirely.
For some of these questions, I have included “Don’t Ask” questions. These are the questions that are so canned, boring, and predictable they should be exiled from good dates.
Our Best First Date Conversation Starters:
Are you working on any personal passion projects?
This is my go-to question and it comes up very naturally if someone talks about
- being busy
- what they do for a living
- any hobbies
It can transition you into a nice, broad discussion about hobbies and how they spend their time. It’s so much better than “What are your hobbies?”
What’s the best present you ever gave someone? Ever received?
If it is around the holidays or one of your birthdays, you can talk about presents. This is also a great one if there is a birthday in the restaurant you are eating in!
What does a typical day look like for you?
Don’t ask, “What do you do?” Instead, ask them about their typical day. This question will give you much more robust answers and you will learn far more about a person than just asking, “What do you do?” You can find out if they are an early riser, how they spend their free time, and, typically, their job will come up as well. I have found that you don’t really need to ask about their career–it usually comes up naturally.
I was reading this _____ and they said____.
I am a big fan of bringing up books and articles on first dates. Here are my favorite books that stimulate interesting conversations.
Is there anything you don’t eat?
This one comes up quite easily if you are ordering food. It can produce some really easy conversation and might provide you with some great tidbits.
What sort of vacations do you like to take?
People often ask, “Have you gone on any vacations recently?” However, someone can answer that very quickly—and they might not have gone anywhere (which results in awkward silence). Instead, try asking what kinds of vacations they like to take. This produces great conversation and ample “get to know you” responses. Talking about traveling can even get you a second date! Professor Richard Wiseman conducted a study and found that 18% of couples who discussed travel went on a second date, compared to only 9% of couples who talked about movies.
Anything surprising happen today?
Don’t just ask, “How was your day?” Instead, ask them about what was surprising about their day. You also can try asking for their high point and low point. This will get you less of a canned response such as “fine” or “pretty good.”
Bonus: You also can use some of our killer conversation starters.
What’s the best advice anyone ever gave you?
Whenever someone shares a piece of advice with me, I typically ask them this question. It is a nice transition that brings up fascinating topics.
Tell me about your closest friends.
Use this if they bring up a friend or a story with their friends. This is a great follow-up question that will help you get to know who they spend their time with.
What were you like as a kid?
Some people ask, “Are you close to your family?” but this can be a bit personal for a first date, and people usually have a canned answer. Instead, ask them what they were like as a kid and let them tell you stories about themself and their family.
Bonus: If you are familiar with Birth Order personality types (highly recommend it), you can ask if they have siblings and talk about birth order—do they fit the typical personality types for their order?
I’ve been watching ____ and love it. Have you seen any good movies or TV shows lately?
This is an easy one, and will give you an idea of their viewing tastes.
Bonus: Which fictional character do you relate to the most?
Have you been to any good restaurants recently?
If you are eating out and talking about the quality of the food/menu/atmosphere, this is an easy segue question to find out their dining habits.
Do you have any pet peeves?
This can come up as annoyances arise (inevitable)—someone is texting at the next table, someone is speaking too loudly across the room, there is a long line…
Bonus: Share Secrets
By sharing personal and emotional exchanges, you can promote connection, according to psychology professor Arthur Aron, psychology professor at State University of New York at Stony Brook. Take it a step further and discuss controversial topics, such as your stance on the upcoming presidential election or veganism. These types of conversations fuel the brain and are far more interesting to us than the typical, dull, boring convos, according to Dan Ariely, psychology professor at Duke University.
Make Great Conversation
These first date questions are guaranteed to make your date go smooth. But once you’re done asking the questions, what next?
Time to take your conversation game even further and focus on enriching your self-improvement skills.
Check out this free goodie today:
Communicate With Confidence
Do you struggle with small talk? Do you often run out of things to say or feel awkward and self-conscious in social situations? Our Conversation Mastery Course teaches you the secrets of master conversationalists and gives you the skills you need to have confident, engaging, and captivating conversations with anyone, anywhere.