21 Conversation Starters & Topics For A Fun Date With A Guy

The Ultimate List of 21 Conversation Starters & Topics For a Fun Date

Conversation Starters & Topics

How to ensure you have a fun and easy-going date with him

How to ensure you have a fun and easy-going date with himConversations can often be a little uncomfortable. Especially if you just met him.

You may wonder:

  • What should you talk about on a first date or second date?
  • What topics do you want to avoid on a date?
  • What are some good first date conversation starters, topics, and questions?

If you don’t think about this beforehand, there’s a good chance you’ll end up in a boring conversation where it’s almost as if you’re exchanging resumes.

And that’s a SHAME if this happens… Just because you don’t know what to talk about on the first date.

You might meet someone who’s your perfect match, but it will never lead to anything because the initial verbal interaction isn’t going well.

To make sure you don’t miss out on (even more) amazing partners…

In this article, I’ll share a list of 21 good first date conversation topics, advice and other things to talk about to make sure you have an amazing time.

Use them during a conversation, in a relationship, or on a 1st date.

Here’s the list of 21 good things to talk about on the first date with conversation tips, starters, questions, and advice.

1. Let him talk

Woman listening while man is talkingAlthough this may seem obvious, it will surprise you how many women talk about themselves the whole time on the 1st date.

They’re trying to convince him to like her and therefore think:

“If I tell him enough good things about myself, he’ll see how nice I am.”

But unfortunately, that’s not how it works.

In fact, he’ll get the impression that you’re desperate. And that’s something men find very unattractive.

Here’s an article with 23 tips on how you make a guy fall in love with you.

Now, I understand that you want to show that you are a nice woman.

But by constantly talking about yourself, you are only doing the opposite.

It’s much easier to have a chat with someone by showing interest in the other person than it is by just talking about yourself.

It’s just like Dale says:

“You can make more friends in two months by becoming interested in other people than you can in two years by trying to get other people interested in you.”

-Dale Carnegie

When you are only showing an interest in him, there will come a point when he thinks:

“Hey, but who is she anyway?”

Suddenly, this makes him a lot more interested in you than if you would just start talking about yourself.

So first, take an interest in him, and then at one point, he’s going to be so curious about who you are. Then he wants to know more about you.

2. Goals and passions

Goals and passions

On first dates, people often talk about it:

  • What are you doing NOW?
  • How’s your job NOW?
  • How’s your life NOW?

That’s because people often tend to talk about the here and now.

Instead, you can talk about his plans for the future.

Great questions to ask a guy is for instance…

ask him what he wants his future to look like.

When you talk about these topics, you often get to know a lot more about each other.

What a person is doing now is the result of the choices done in the past.

And the choices he makes today ultimately determine his future.

Besides that, it’s just fun to hear someone talking enthusiastically about his passions.

In other words, goals and passions are excellent conversation topics.

3. Family

Family

OK, maybe not the best subject in this list to talk about on a date. But when it comes up, talking about family is an excellent topic to discuss.

Parents. Brothers. Little sisters. It’s plenty of things to talk about.

Do you have little kids in the family? Then talk about that. A man is more attracted to a woman he thinks would make a good mother. So this is a very subtle tip that will make him like you more.

Make sure you don’t talk about family dramas or other heavy emotional topics, this will scare off a lot of guys.

4. Superheroes

Superheroes

Superheroes? Yeah, superheroes.

I know, this one may sound a little crazy, but every man – whether or not he dares to admit it – has one.

His superhero can be anyone: Batman, Spiderman or maybe even his mom.

Just say:

“Hey, perhaps it’s a bit of a weird question, but who’s your superhero and why?”

Childish? Unless you have a complete deadbeat in front of you… Every guy can laugh at this, and with the biggest smile on his face, he will tell you who his superhero is.

But don’t be surprised if he later asks who your superhero is.

5. The name game

The name game

The name game is always fun to do on a 1st date.

It adds some variety in a conversation and is therefore ideal for brightening up a (too) serious conversation.

How does this work?

  • Ask your date if he thinks his name suits him.
  • If so? Ask why.
  • If not? Ask what name he thinks suits him better.

This is a playful way to have a little more fun if you notice the conversation is getting increasingly boring. Save it by throwing in the name game (before it’s too late).

If you want some more inspiration with great things to do on a first date, read this article.

6. Life lessons

Life lessons

By talking about life lessons, you add more depth to the conversation.

Ask him about his life lessons from the past few years, and I guarantee he’s got plenty to say about it. 

The great thing about life lessons is that it shines a light on positive things. Because his experiences can be positive or negative, but the lessons he learned are always positive (and if his life lessons are negative, you know that he’s a guy with emotional baggage).

In other words, life lessons are a fun way to get to know each other.

7. The Lilla list

The Lilla list

You probably know someone around you who somehow always manages to keep the conversation fun and always going.

When the conversation almost comes to a standstill, he has a question to keep it flowing.

It’s like magic. But rather than magic, it’s just a matter of proper preparation.

A good friend of mine, Lilla, is such a person. Whenever a conversation is about to get boring, she manages to breathe new life into it.

Her secret?

Perfect 1st date questions.

She has a questionnaire on how to get to know someone really well in an entertaining and captivating way. Amazing 1st date questions.

Curious about what these questions are? In this article, you’ll find no less than 101 questions that will help you get to know each other better. I recommend that you keep some of them on your phone and then check them out when you go to the bathroom.

8. Travel and holidays

Travel and holidaysThis is always a great topic to talk about on a first date.

Why?

Well, look:

  • Everyone loves vacations.
  • Everyone has incredible travel memories.
  • Everyone has several holidays scheduled in the future.

So by talking about going on holiday and traveling, you often have a wonderful conversation.

One piece of research even shows that just by talking about holidays and travel means there’s an 18% chance of a second date. That may not seem like much, but it is. So unless you hate vacations, it’s a good idea to talk about it.

Bonus tip: ask him: “If tomorrow you could go on holiday anywhere in the world, which country would you pick, and why?” With this simple question, you get to know each other quickly, and at the same time, you are having a fun and light conversation.

9. Teenage years

Teenage years

You most likely have a lot of embarrassing memories from your teenage years.

The funny thing about these memories is that you thought these were terrible at the time. But now that you’re older and wiser, you are probably laughing about it. Because your teenage problems are nothing compared to the difficulties you’re facing as an adult.

And just to mention it, adult problems is another topic you want to avoid at all costs on a first date.

But teenage problems?

“Teenage problems are just funny first date questions and often even a little adorable…”

Teenage problems

Talking about these on a first date often leads to a hilarious conversation. Besides, you also get an idea of what he used to be like.

Some things you can ask and some funny first date questions are:

  • What’s your most embarrassing teenage memory?
  • What was your greatest night as a teenager?
  • What’s your funniest memory as a teenager?

10. Secrets

Secrets

Let’s say you are sitting in the quiet zone on a train. Then you lean into your friend next to you and say that you have a secret you want to share with her. I can guarantee that half of the other passengers will try to listen in on what you are going to say. (the other half is probably too busy with their smartphone).

There’s just something about secrets that makes everyone curious. So it’s great to tell each other some secrets during a first date. Research even shows that these form a deeper connection.

It’s just good, fun and deep first date questions that help you get to know someone deeper.

So say to him playfully:

“Hey, I don’t even know why I’m telling you this, I don’t usually tell anyone, but… (tell your secret here) …”

And of course, you don’t have to reveal your deepest secret. But saying that you’re afraid of spiders, for example, can get an exciting conversation going.

And afterward, you can challenge him to tell a secret about himself.

Looking for a complete list with the most important things for women to know for a first date? Read this article.

11. Career

Career

This is one of the trickier topics on the list.

Because look. Most men find it attractive when a woman has a job she likes and that she’s ambitious.

But a woman who talks about her work all the time?

We don’t like that very much.

So with that said, talk about each other’s careers briefly in the beginning. And if he wants to know more about it, he’ll simply ask.

Save the gossip about your boss and colleagues for another time.

12. The surroundings

The surroundings

This may sound a little crazy, but your surroundings are one of the most fun conversation topics there are.

Maybe you haven’t read my first date tips yet, and you’re planning to go out for dinner or a drink together. In these two scenarios, it will be challenging to talk about your environment.

But if you’ve chosen one of my 23 ideas for a first date, then you can talk about what’s around you for hours. If you decided to go to a petting zoo, for example, then there’s plenty to see and do.

So if the conversation comes to a standstill, mention something cool in your surroundings, and talk about that.

13. Your opinion

Your opinion

This topic may sound a little strange. I don’t mean you should have an opinion about everything all the time (that’s annoying).

The reason I mention it here is because a woman without an opinion is one of the biggest turnoffs for men. And honestly, a woman without an opinion doesn’t even exist; everyone has one.

So make sure that you share your opinion every now and then on the first date. It’s even better to be a little controversial than to pretend you don’t have a viewpoint about anything.

So keep that in mind, and you’ll be fine.

14. Lucky clothes, talisman or superstition

Lucky clothes

I’m sure you know someone who’s firmly convinced that his shirt will bring good luck. Whether it’s lucky socks, pants or a sweater… One thing is certain: behind every lucky garment, there’s a great story. And the same goes for other things that people are superstitious about. Even weird rituals or other things that are supposed to bring luck.

Everyone has got some of those crazy little things and often with a whole story behind them, along with a unique experience. If not? Then just proceed to the next conversational topic in the list.

15. Movies and books

Movies and books

Nearly anyone can talk about books and movies.

OK. I admit that not everyone reads books.

But there are hardly any people who don’t watch films or read books.

Some things you can ask about it is, for example:

  • What’s your favorite movie?
  • Which book made the most impression on you as a child?
  • What’s that one book you know by heart from back to front?

The great thing about talking about books and movies is that it says a lot about a person. Because if he watches cartoons twice a day at the age of 35, you know what kind of “guy” you have in front of you.

Besides, talking about movies and books is almost always fun.

16. Free time

Free time

You probably saw this one coming.

He has 24 hours a day, and how he spends that time says a lot about him.

So suppose you’ve found out he’s not a workaholic (conversation topic #11). Then it’s obvious to ask what he does in his spare time, right?

Not so fast…

It’s much more exciting if you make a statement to him.

For example:

“You seem like the type of guy who spends a lot of his spare time in the gym.”

The cool thing about this is that it provides variety in your conversation since you’re not constantly asking questions. Yet, he’ll almost feel obliged to answer. Win-win.

17. Achievements

Achievements

Granted, this topic sounds a little interview-like.

But come on, when it’s your first date with him, you want to know what he’s made off.

Besides, men love to talk about things they’re proud of.  

So just ask:

“What are you most proud of?”

Not convinced yet? This is what relationship expert Wendy Walsh has to say about it:

“It’s a great, intimidation-free way to get a sense of a person’s values and what’s important to them.”

-Wendy Walsh, Ph.D.

In other words, this is a simple way to (re)start a conversation.

And knowing what to say on the first date that can make you feel more at ease.

18. Food

Food

By “food,” I don’t mean dietary tips, nutrition goals, or calorie intake. Unless there’s an elite level athlete in front of you, these aren’t the best topics mention.

Ask him what his favorite dish is, and I don’t mean in the boring “what’s your favorite dish” way, but ask:

“What food can I wake you up to 6 in the morning?”

The romantic thing about this question is that he will now imagine you coming and giving him his favorite dish at 6 in the morning.

Another fun question is:

“What is your most triumphant food victory?”

Maybe he has taken part in an eating contest, or perhaps he fixed the Christmas dinner for his whole family last year.

In short, this is a funny topic to talk about, and everyone has something to say about it.

19. Music

Music

Music can be a great conversation topic to start the first date with if you do it right.

Don’t just ask about his favorite band. That’s boring.

It’s more fun if you ask:

“Name a band you used to be crazy about, but now you hate?”

Every time I ask this question, a long conversation follows.

This question is also a fun way to use as one of those…

that really help you to break the ice.

20. Childhood years

Childhood years

Not everyone’s childhood has always been fun, but something positive has undoubtedly happened in his youth.

So ask him about that.

It is also good to ask which people were the most important to him in his childhood. In most cases, he brings up a bunch of people that meant a lot to him. It’s a perfect way to get to know him well.

If he tells one of these stories with a smile on his face, encourage him to keep telling more by asking follow up questions.

He’ll ask you the same question afterward, so be prepared 😉

21. Friends

Man spending time with friends

I’m sure I don’t need to explain to you that it’s too early to start a relationship on a first date (duh).

But if things actually work out between the two of you, you’ll not only have a relationship with him but also with his friends.

And friends say a lot about who he is. If, for example, he tells you that his friends are doing drugs at festivals every week… Then you can be sure that he does the same thing.

And suppose that’s not your thing (which I hope), then you know it’s the right time to thank him for the date and say goodbye.

All you need to say is,

“Hey, tell me about your friends…”

He often gets really excited when you mention this. He likely has so many fun stories to tell that he doesn’t know where to start.

If your date with him turned out amazing and you want advice on how to text the guy to make him fall in love with you, read this article.

Share

Tim Veninga

Tim Veninga

Tim Veninga is the head coach of Change Him. In The Netherlands more than 155.000 women follow his advice. He has been featured in numerous Dutch media and magazines like Cosmopolitan and Glamour.
Connect with Tim:

Leave a Comment

Your email address will not be published. Required fields are marked *

Scroll to Top