How To Keep A Conversation Going With A Guy? 10 Tips

Okay, so you’ve met a great guy that you really like. But how do you keep the conversation going so that he doesn’t get bored?

The art of conversation is something we all pick up from childhood. We listen to the way those around us interact, and we understand quickly how it works. We start to talk to our friends on the playground, and fine tune our techniques so that we get out of the conversation what we want.

Some people are just better at keeping the conversation going than others. A lot of the times it’s a combination of confidence, experience and wit. But you know what? Learning how to be a good conversationalist is easy! It’s simply a case of knowing a few tricks so that you’re not left stuttering your way through a conversation until you fall into absolute, deafening silence because you really don’t know what to say next.

With a bit of practice, you can become a great conversationalist who guys finds super interesting. Let’s take a look at 10 tips on how to keep a conversation going with a guy.

Always Be Positive

You know what is one of the biggest conversation killers? Negativity.

Let’s say you tell a guy that you’ve got a problem. He enthusiastically presents a solution that he knows will work.

However, you dismiss it out of hand. You won’t even let him finish because “it’s pointless – it won’t work.”

He sighs and gives up. You won’t even hear him out. Your pessimism killed it.

And what if you keep complaining the whole time to him? Pretty soon he’s going to get bored, drink his drink, look away and say “Aha”.

If you are positive about everything, it’s so much easier to keep the conversation going. The good vibes will rub off on him, and he’ll stay interested.

Ask An Open-Ended Question

A close-ended question is one that can be answered with a simple Yes or No. Or, worse still, a I Don’t Know.

Or, in fact, any a single word will do. It doesn’t leave much room for the conversation to progress.

For example, you might ask “what’s your favourite colour?” and they might answer “blue.”


Great conversationalists are all too aware of the power of asking good questions. Questions can change the entire complexion of a conversation, inspire debate, bring people closer together, and ultimately get you closer to where you want to go.

Ask questions that you know will demand a more elaborate answer.

Figure Out Quickly What He Likes To Talk About

After a while, you will notice a pattern: There are some topics of conversation that he gets excited about, and others that see him sink into his sink and reach for his phone.

Quickly work out what he loves to talk about and keep the conversation in this ball park.

Plan Ahead

You can’t really plan a how a conversation will go before it happens, because conversations take on their own life. They veer off in all kinds of directions.

However, having a few topics in mind that you wish to talk about before you meet the guy acts as a safety net in the event that things go quiet.

Have you ever said to someone, “there was something I really wanted to ask you today but I’ve totally forgotten what it was”? Planning what you want to say beforehand means you won’t need to have these moments.

When the conversation looks like it’s dying, recall the topics you had in reserve and bring one up.

“Oh! By the way …”

Be Willing To Open Up

If you’re extremely guarded throughout the conversation and are unwilling to give anything away about yourself, you’re going to find it hard to keep the conversation going. He asks a question and you coyly say, “I don’t know,” before asking if you can change the topic.

Be willing to open up. Show him that you trust him. Otherwise, he’ll get the impression that you don’t trust him – and that can really kill a conversation.

Ask For More

Did what he just say sound super interesting? Then our next tip on how to keep a conversation going with a guy is to ask him to tell you more!

Compliment Him

It’s important to remember that there are two people in this conversation, and you might not be the only one who’s feeling a tad nervous and apprehensive. If he’s feeling the pressure too, sending a compliment his way is an easy way of relaxing him and loosening him up.

A compliment not only gives him a shot of confidence and brings him into the conversation, it could also kickstart a new topic. For example, you might say “I really love your shirt. Where did you get it? Do you think fashion is important by the way?”

Ask Him To Tell You Something About Himself

Another easy way to kill a conversation is to constantly talk about yourself. By directing the questions at him and his life, you’re giving him a platform to do what he loves to do – talk about himself!

Unless a guy is super, SUPER shy, he’ll enjoy talking to you about himself.

“What do you wanna know?” he’ll ask, as he eagerly sits forward in his chair and clasps his hands together.

Take A Look Around

Okay, so the conversation is totally dying and you can’t remember any topics you had in reserve. It’s almost time to start panicking. What do you do?

At this point, it’s important that you try to remain as calm as possible before taking a look around you. Is there something that grabs your attention that you could quickly mention? Maybe you could talk about the weather or even the location. Or how about the food you just ate? If you’re drinking coffee, why not bring up a really funny anecdote, such as the time you drank five cups of coffee in two hours and couldn’t sleep for three days?

Avoid The Dreaded One Word Answer

Always be prepared to elaborate. Give him something to feed on.

How to keep a conversation going with a guy? What are your best tips?

Stay happy!

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