First date conversation tips

What to say and what to ask on a first date

You are going on a first date, and now you are wondering about the best first date conversation tips. Great question, because an amazing conversation will lead to mutual attraction and a deep connection between you and your date.

Be a great listener

Let me break it down for you, the hallmark of a great conversationalist is not what they say; it’s how they listen. To be an absolute treat for your date, you just have to be present and intensely listen to what they have to say.

There is a bit more to it, so keep on reading, and I promise you will be prepared to wow your date.

Ask stimulating questions

Without the right questions, it’s hard to be a dazzling conversationalist. This is true for your date as well as between friends. So plan a couple of cool questions and think about great first date conversation tips, and you will kill it. Nothing wrong with being prepared.

Without the right questions, the conversation often stays at the surface level. This means two people exchanging facts rather than opinions and feelings.

Give them a chance to show who they are

The right question, on the other hand, can really make someone open up.

When you do ask more complex questions, remember that most people enjoy sharing their opinions and feelings. You are not intrusive; you give them a chance to show you who they really are.

Being well prepared with a couple of interesting subjects is even more important if you or your date (or both) are more introverted. Here are our splendid guide Dating for introverts, to further help you nail that first date.

Find out more about his passions and interests

Start the date by asking a couple of questions aimed at finding out what things your date is passionate about. What are his biggest interests? What is his reason for existing, and what does he want to achieve with his life?

You can ask a question similar to “What are the five things you want to experience before you die?“

Be playful

If things get serious quickly, just handle the situation with playfulness and a laugh. Acknowledge the elephant in the room and make a joke about things getting deep really fast.

Also, tell him that, on a more serious note, you enjoy finding out what makes him unique.

Show him that you are fascinated by him

The right questions are one part of being a memorable conversationalist. The other equally important part is to be present and listen. Don’t think about your replies, don’t think about the stuff that’s going on in your life. That is my second and very important first date conversation tips.

Give him non-verbal clues

Just relax and take in every word he is saying. Laugh when he is being witty or funny. Nod your head when you agree with what he is saying. Give him a mischievous smile when he tells you something out of the ordinary.

Basically, give him lots of non-verbal clues that you enjoy listening to him and find what he is saying interesting.

Stay present

Most people are not expressive enough when they listen to another human being. Most people are also not present enough, so the more present you can be, the more you will stand out from all his other dates.

The date and the conversation are also about you

Now when we have your listening skill under control, we need to move on to another equally important aspect; you.

Being a great listener will get you halfway to an amazing first-date conversation, but my next tips is about you.

Share and be vulnerable

For someone to be able to connect with you on an emotional level, they need to find out things about you. They need to understand you. They need to get the feeling that they are invited into getting to know you on a deeper and more personal level than most people.

Sharing is an important part of building a connection. That’s how the two of you create something unique together.

Invite your date to get to know you by being vulnerable

One part of creating attraction is to be vulnerable and personal. You can tell your date about struggles and sad moments, but for things to not get too heavy, try to be pretty upbeat and positive. No one wants a complainer for a first-date conversation.

With this little caveat out of the way, let’s try and dig a bit deeper.

Tell new stories

Don’t have the same type of conversation you had with your last date. Challenge yourself. Tell stories you haven’t told before. Try telling the stories you often tell in a new way.

A great conversation is an exploration into our past and how we regard life’s big philosophical questions. We should also connect those dots to our future, and who we strive to become, and the goals we want to achieve.

A great conversation is two people exploring the world together through words

But to be a great conversationalist you can’t do this as a monologue. You have to allow the other person to be the inspiration behind discoveries and conclusions you make. The other person should be your guide to discover new things about yourself and new ways of looking at your past.

Sounds complicated? Just practice, and you will become better at this. Share things about your past, but in an upbeat, constructive way.

Ask yourself what makes a conversation memorable?

Also, take some time and think about the great conversations you had with friends. What were you doing at the time? What made the conversation great and memorable?

This way, you find out more about what kind of subjects you enjoy and what conversations make you all fired up and happy. That’s my third first date conversation tips; find out what kinds of conversations you enjoy.

Ask him to tell you something that’s a secret

We all have the things we usually talk about. But to make the two of you form a strong and unusual connection, you have to talk about something both of you usually don’t talk about.

We all have secrets. Your date has secrets. Now is the time to find out one of them and to give this secret proper attention.

Dig a bit deeper

This doesn’t have to be your traumatic childhoods or the time you were fired from your job. Those subjects are better to save for the second date. Check out my second date advice here.

The secret could be something fairly innocent. It just has to be something the other person hasn’t talked about in a long time.

It can be a secret aspiration of theirs or some amazing long-forgotten memory from their childhood. Just something that unlocks a room whit in them that they don’t often visit.

To reach this place, you can ask this question or something similar;

Tell me something about yourself most people don’t know?

Ask him about his shortcomings

This is a sensitive subject, and a lot of men are going to be uncomfortable talking about it. But the truth is that when we tell someone something vulnerable about ourselves, we actually feel closer to that person.

We have trusted them with an important part of ourselves, and as a direct result of this, our trust for them becomes stronger.

Examples of a good question to reach this part of him can be;

What have you learned from the setbacks and failures of your life?

But do keep it positive

Make sure that you frame the question about his shortcomings in a mostly positive way.

How did he handle his problem? Did he learn something important? Did he come out stronger on the other side? Would he have done something different regarding the problem as the person he is today?

You might feel like all of this is a lot of work, and on top of that, the result is hardly guaranteed. If you have doubts, read our article Is online dating a waste of time?

Don’t be afraid to disagree

Sometimes when we go on a first date, we are just too pleasant. Don’t fall into this trap. A playful discussion is fun. Providing him with a challenge is my fourth first-date conversation tips.

Showing the other person that you can disagree about things without becoming too emotional actually shows them that you are a cool person to be around.

Disagreement creates a lot of sexual chemistry

Flirty banter is just the best when you want to make someone attracted to you. So, go ahead and challenge him when he says something you disagree with. We all enjoy a bit of healthy resistance. Check out our article How to tease your crush, for more ideas.

Show him that you have opinions you are passionate about.

Connect by finding similarities

Great conversations are also about finding things both of you like. When we find common ground with someone, we instantly feel closer to that person.

Do bring up books, movies, and songs you like. Also, ask about what he likes when it comes to those areas. If you find something you both really like, show him that you are genuinely happy to have found common ground.

We like people who likes the things we like

When someone shares our taste, it confirms that we have made a good choice and have great taste. This is important for humans since we are social beings. In modern society, our cultural choices are a way we define ourselves against the rest of the pack. Also, it is just plain fun to discuss something both of you are passionate about.

The things he likes tells you a lot about him

When you do find out what he likes, ask him why he likes those specific things. Ask him why that book or song speaks to him? In what way has it changed him and his life? This way you will find out a lot about him.

If the conversation or chemistry take a dive; change location

Sometimes the conversation just keeps staling, and nothing you do seems to help. When this happens, it is time for some physical movement to change things up. Suggest going somewhere else to check something out or for a drink or a coffee.

A new location will give the two of you the impression of having known each other for a longer amount of time, thus being more comfortable with each other. A new location will naturally lead to new conversations subject since you have new things to observe and comment on.

Move to make the conversation flow

The motion of physical movement is also a good way to relax and open the floodgates to more amazing conversations. Many people find it easier to talk and connect when they sit or walk side by side, rather than sitting opposite each other. So when you arrive at a new location, you can try sitting next to him.

Here are three more great questions to ask?

What book has had the biggest impact on your life?

If you could meet a famous person, who would you choose?

If you could re-live six months of your life, which period would you choose?

A Final note

In this text, I have given you plenty of questions to ask on a first date. More importantly, I have also explained why those questions work and lead to great first-date conversation.

My final tips are to use those questions for inspiration, but you should also take some time to come up with questions you think are interesting.

This way, the questions you ask your date are uniquely tailored to who you are and what your interest is. The conversation will naturally be one you enjoy, and that enjoyment will make your date feel great about himself. A double win.