What to Talk About with a Guy: 10 Tips to Hold His Interest

She knows exactly what to talk about with a guy to keep him interested

“Men are easy. All they want is sex.” It’s an old trope we hear repeated so often we could be forgiven for thinking it’s true. In reality though, that’s just not how things work. You may very well find yourself stuck for ideas around what to talk about with a guy on a date and that’s okay.

If that’s where you’re at right now,, you’ve landed on the right article. As a guy that’s very familiar with the dating scene, I can assure you of two things. Firstly, men aren’t quite as complicated as it can sometimes feel (but also not as easy as stereotypes suggest).

Second, this article will give you the tips you need to make conversation easy on every date.

Dating Conversation Made Simple: What to Talk About with a Guy

Modern dating is all about getting to know each other quickly. We’ve grown accustomed to having a wide range of options at our fingertips and moving on quickly if things don’t feel great.

It makes sense, then, that we’re all like this with our dating choices too. If conversation is dry and difficult or we’re just not having a good time, we move on to the next one and never look back.

Whether you’re struggling to land that second date or just looking to make the process easier, here’s what you need to know.

A couple of basics that apply to every date

First things first, here are a couple of things you should be doing on every date to help you along. They’ll make sure you know how to keep a conversation going with a guy in any context.

As you get better at it, you’ll become more effective at steering that conversation. Although if that much work is required, you could probably do better than him. It had to be said.

Conversation threading makes for infinite conversation

If you’re not familiar with conversation threading, it’s something worth reading up on. I mention it in quite a few of my articles for a good reason. Once you get good at it, you can carry on any conversation in any context, easily.

In short, it’s about recognizing the different topics within a sentence he says. A single sentence could offer up four different tangents for your conversation to go down. All you have to do is ask him a question about it or relate with a similar story of your own.

Take this basic example:

“I wasn’t sure if I was going to be on time tonight. My car broke down on the way from work!”

From that one statement, there are several directions you can go.

  • You thought you were going to be late? And miss this? [Gesturing to yourself]
  • Oh no! I had a flat tire leaving work the other day too. So frustrating.
  • What kind of car do you have?
  • Where do you work?

The list could go on but you get the point. With a little practice, even the most mundane of responses gives you a host of topics to respond with. When this becomes second nature, you’re never left stuck for words

Keep your conversation light and fun — no politics allowed

This is a trap that’s more common than you might think. Especially if it’s a first date, it’s about having fun while you get to know each other. Rather than talking about politics and religion, show off your personality and sense of humor.

If he starts complaining about work, acknowledge it then change the topic. It’s okay that he brought it up but you don’t want to dwell on it or feed into that conversation.

The number of times I’ve had this on a first date is astounding!

What to Talk About with a Guy: Topics to Get You Started

With those out of the way, let’s take a look at some specific examples of how to talk to a guy. You can literally take this list with you if you’re feeling that nervous. But I have more faith in you than that even if you don’t!

Ask about his interests

“So you mentioned you were playing basketball the other day. When did you start?”

This sounds like a boring question, I know. The thing is, if it’s a sport he’s really into, he’ll be excited to talk to you about it. Even if you don’t give a damn about basketball, you’re about to learn much more about him than just the sport anyway. Even if you misunderstood and he doesn’t actually play, he’ll probably tell you what he does like instead.

When someone wants to talk about something they’re passionate about, it's easy to be engaged.

Recent vacations make for exciting stories

Rarely does anyone return from a vacation going “eh, it was okay. Nothing worth talking about.”

You can start by talking about something that happened on one of your recent adventures. From there, ask him where he went last. Almost every time, he’ll tell you where he went and immediately launch into story time about something fun or disastrous.

Either way, it’s such an easy topic to share stories about — good or bad.

It’s okay to talk to a guy about his career

I know, I know. We’re all sick of “what do you do for a living?” on the first date. Firstly, it’s a common question because it tells us a lot about the other person. An oil rig worker is probably (not always!) a very different type to a lawyer. Not necessarily better or worse, just different.

The other reason I don’t mind it is when you push past what they’re doing right now. Talk about what motivates them and where they’re going with it. As someone that’s excited about my own career path, I find it intriguing to hear about others.

About where they want to end up with it and what got them started in the first place. Think less about “what building do you work in” and more “what makes you get out of bed in the morning.”

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Ask him what he thinks of some of the things you like to do

This is a question you know you can easily engage in and it’s an interesting one he may not have heard before. If things are going well, it’s also an ideal segue into initiating another date.

Whether it’s a sport, hobby or a quirky tradition you have with your friends, find out if he’s into it. If he is (or he’s at least willing to give it a shot), go ahead and make plans to try it together some time.

There’s something so fun about flipping that usual gender expectation and having a date teach me something new. I like it and there’s a good chance he probably will too.

You can always talk to a guy about online dating stories

It seems most people have some kind of online dating horror stories. Personally, I love these as a first date topic. More importantly to this topic, they’re stories that people get very emotive about as they’re telling it.

It seems as though some people out there, men and women, are straight-up crazy. You won’t believe some of the stories you hear and that’s exactly the point. How fun!

What are you looking for from dating right now?

If the two of you are at a stage where real talk can be introduced, why not start with this one?

Personally, I’m a fan of cutting to the chase. I don’t want to go on several dates with someone only to find out our intentions don’t line up. Instead, you can drop this one into the conversation verbatim.

Now, be careful with the delivery on this one. It’s a real conversation but that doesn’t mean it has to sound too serious. You can still have this chat while keeping a lighthearted tone. Remember how I said you want to keep it light and fun? That can still apply to this question too.

If you get really stuck you can use the menu as a crutch

As a last resort, wherever the two of you are probably has a menu of some form. Particularly if you’re at a themed bar or restaurant, there’s probably at least one thing on the menu neither of you have tried. Whether it’s a cocktail, exotic food or some odd combination, ask him if he’s tried it and if he’s down to take a risk together.

This one might also sound lame but don’t be fooled. There’s something oddly exciting with taking a risk sometimes. Getting adventurous like this is how I first tried beef tartare and as it turned out, I loved it.

On that particular date, neither of us had tried it but were intrigued. Raw beef and egg sounded like a risky choice so the nerves were there. We chatted with our server about it for a moment (great buffer), took the risk and were anxious to see it come out.

Always keep this up your sleeve in case you’re stuck for words!


See, finding things to talk about with a guy isn’t as difficult as you thought, huh? There’s no magic involved in dating conversations, just keep it interesting and avoid getting too deep. That comes later.

If nerves get the best of you sometimes, that’s okay too. Just bring it back to these basics and you’ll be totally fine!

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