The Ultimate List Of 21 Things To Talk About With A Guy

The Ultimate List of 21 Things To Talk About With A Guy On A Date

Things To Talk About With A Guy

How to never run out of things to talk about when you’re on a date with a guy

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 with a guy?
  • 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 things to talk about with a guy.

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 an amazing guy…

In this article, I’ll share my ultimate list of 21 things to talk about with a guy to make sure you don’t have a boring time and never run out of things to say.

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

Here’s the ultimate list of 21 great things to talk about with a guy:

1. Let him talk about whatever he wants to talk about

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.

Now, I understand that you want to show that you are a great 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 who is she anyway?”

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

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

2. Goals and passions

The Ultimate List of 21 Things To Talk About With A Guy On A Date 1

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, 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.

Here are some questions you can ask him to find out his career ambitions:

  • Why did you want to become [insert job here]?
  • How did you end up becoming a [insert job here]
  • Why do you study [insert job here]?
  • What is your goal with [insert hobby here]?

3. Family

The Ultimate List of 21 Things To Talk About With A Guy On A Date 2

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.

If you’re curious to know if he genuinely likes you and not just being nice, then read this article.

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

Here are some questions you can ask him about his loved ones:

  • Do you have any sisters or brothers?
  • (as a follow up) Are you guys very similar? Why?
  • How did you grow up?

4. Superheroes

A woman's ability to forgiveness shows how strong she is.

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 dad.

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 is always fun to do on a 1st date.

It adds some variety to 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

The Ultimate List of 21 Things To Talk About With A Guy On A Date 3

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.

Here are some questions you can ask him about his previous life lessons:

  • What is the most important life lesson you have learned?
  • (when speaking about a subject) So was there anything you learned from it?

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?

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 only look at them 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.


Well, look:

  • Everyone loves vacations
  • Everyone has incredible travel memories
  • Everyone has some holidays planned 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 you could go on holiday anywhere in the world tomorrow, which country would you pick, and why?”

You can also ask him:

  • What is the most amazing place you have visited? And why?

With these simple questions, you get to know each other quickly, and at the same time, you are having a fun and light conversation.

9. Teenage years

Laugh at his jokes (even if he's not funny)

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

The funny thing about these memories is that you thought they were terrible moments when they happened. But now that you’re older and wiser, you are probably laughing about them. 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 topics and often even a little adorable…

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?
  • I’m curious… how were you as a teenager?

10. Secrets

Leave a trace of mystery behind

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 make you form a deeper connection with each other.

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.

11. Career

The Ultimate List of 21 Things To Talk About With A Guy On A Date 4

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.

I’d add that if you want to talk about it, try to find out things about him as a person (not details of his career). For example, ask him why he does what he does, or what he enjoys most about it. Then try to find a link from this to his personality. You could for example say: “It sounds like you’re the type of guy who really likes to help others”.

12. 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 26 must-know first date tips for women 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 and activities 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

Mirror his movement

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

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

The Ultimate List of 21 Things To Talk About With A Guy On A Date 5

Nearly everyone 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?

Don’t forget to ask him WHY he’s passionate about these books or movies to learn more about him deep down.

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

The Ultimate List of 21 Things To Talk About With A Guy On A Date 6

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.”
  • “You seem like the type of guy that knows everything about [subject].”

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


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

Make him think it's his idea

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

Couple on a concert

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

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 stories 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.

This was my ultimate list with 21 things to talk about with a guy

Make sure that you check out this article on how to text a guy to make him fall in love with you.

So that you don’t come across as desperate, or needy when you text him before and after your date.

(I first published this article on my Dutch website here)


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Tim Veninga is a dating coach, relationship coach and social psychology bestseller author from the Netherlands.  He has been featured in media like Cosmopolitan, Glamour, Marie Claire & Elle.

Hi, I’m Tim Veninga. Since 2008 I’ve been coaching men and women to archieve succes and happiness in their love lives.

For years I’ve only been writing in Dutch, but in 2019 I started writing in English as well after many women asked for it.

If you want to get started learning the best of my advice, I recommend you download the 5 texting mistakes most women make.

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