Some people just seem to be good at Conversation, don’t they? And being able to start and sustain an interesting conversation is very much a life skill and – as we’re a manly man site here – a big man skill too.

The good news? Being able to make an interesting conversation in any situation is actually not that hard. There are a few basic skills to understand, and a few things to bear in mind when you meet a person.

Being able to hold an engaging conversation is useful for so many reasons, from networking or building rapport, to getting to meet girls – or whatever else you might need to do.

So how can you be an interesting conversationalist?

1. Ask them about them

The first thing everyone should know about starting a conversation is that people like to feel like they’re the focus. Now, this might not apply in every situation, but in most social settings this is very much a power move.

The trick is to ask people interesting questions that they want to answer…

• What do you think about [subject]?
• Have you got any plans to travel this year?
• What’s your favourite flavour of ice cream?

All of those conversation starters give your subject an opportunity to talk about their favourite subject. Themselves.

Now, you don’t necessarily want to listen to someone talk about themselves all day/night. But, this is a very useful trick if you want to build rapport and keep the conversation going.

2. Active listening

Most conversation is actually listening. And that means not butting in with your own anecdotes as soon as possible, or glazing over while your subject talks about their dog or whatever.

Active listening is a strong tool in your conversational arsenal. It shows that you are interested in what they are saying and that you are paying attention.

So what is active listening?

• Maintain eye contact
• Respond appropriately (nod at certain points, use sympathetic facial expressions or occasionally express your agreement, disgust etc with vocal validations such as ‘Oh really’ or ‘That’s terrible’)
• Confirming back what people have said – ‘So they really said to you that you can’t be an astronaut?’

3. Avoid asking them about work or money

Yes, we all work and yes we all need to make money. But don’t ask about it, cos that is, frankly, boring.

In conversation, someone might mention that ‘in my line of work’ and then it’s usually a good idea to ask for clarity, ‘Oh yeah, what do you do?’

But by leading into a conversation with ‘what do you do for a living’, you’re instantly launching into a fairly boring line of chat about their work. And that conversation can quickly get stale.

Instead try and ask them…

4. Find the fun angle

When you want to create an engaging conversation, the thing you most want to do is get someone talking to your about their passions.

This not only presents their more fun side, but will also help present you as an interesting person (as you’re interested in their interests – geddit?)

Some great ways to find the fun are to ask people things like:

• Where is your favourite place in the world?
• If you could only eat one cuisine for the rest of your life, what would it be?
• Whats the last crazy thing you did?
• Whats your life goal at the moment?

You can see how all of these could lead into a lot of interesting chats, and may even present themselves with opportunities for more interesting conversation.

Although this might sound like casual conversation, it can also work in a business or networking setting too – with some tweaking.

Business angles of the same conversations above might be:

• Do you get to travel much?
• I’m looking for some new restaurant recommendations – do you have a favourite?
• What’s the craziest thing that happened to your business/in your work?
• Do you have any projects on the go at the moment?

5. Laugh at their jokes

Want people to like you? Laughing at the jokes is pretty much route one to building rapport.

Better still, engage with their jokes. Hit them with come back lines.

Having fun and enjoying a joke together is always going to be a great way to make an interesting conversation even more engaging and interesting.

A little tip though: Be sure that their jokes ARE JOKES. There is nothing worse than laughing at someones comment only to realise that it’s not a joke. This also tallies up with number 2 about active listening.

6. Use your sense of humour

Now, this is a harder one to do naturally. But when it comes to interesting conversations, people love to chat to people with a good sense of humour.

The best way to be naturally funny in a conversation is just to relax and be happy and open minded. Easier said than done in some circumstances, for sure. For example, at a business conference everyone is often focused on talking quite mundane business chat. Or in a Zoom meeting, it can be hard to convey your sense of humour.

But being relaxed and offering your insight in a natural manner can be a very powerful way of making interesting conversation.

7. Tell stories

Most of our methods to make an interesting conversation have been mostly focused on your subject until now.

But if you want to really engage with people, and have them find you interesting, is to tell them your stories. This means that rather than saying, ‘Oh yeah I love pizza’, you could tell them a fun story about the time tried to make a pizza at home and you accidentally turned it into a cake with pepperoni on top.

Or, rather than saying, ‘Oh I love to go skiing too’, you could regale them with an anecdote about an experience you had in Tignes.

Bonus points if your interesting stories have a funny twist, are slightly embarrassing or reveal something about yourself.

Now, I would add the caveat that these stories should be true. But hey, that’s up to you.

8. Ask ‘numbers based’ questions

An interesting method employed by Jerry Seinfeld to build up a conversation, especially at the start, is to use numbers based questions.

This means to ask questions that have a specific answer:

• How many years have you lived here?
• When did you last go on vacation?
• How many shirts did you try on before you chose that one?

Asking questions with numbers based answers usually allows you to gauge the conversation and you might even find other subjects to talk about.

9. Speak slowly and clearly

It can be quite easy to speak fast, especially in stressful situations. But by taking your time when you speak, and even embracing pauses, people are more likely to pay close attention to what you’re saying.

Another benefit of speaking slowly is that you’ll often make people feel more relaxed, which can even allow you to dictate the pace and direction of the conversation.

If you’re telling an anecdote, or explaining something, embrace pauses. A pause gives you the moment to find the right word, but also gives people time to process what you’re saying.

10. Change the conversation

Sometimes a conversation gets boring. It happens.

The art of making interesting conversation is spotting this moment, and knowing when and how to change the direction of the talk.

Let’s say your talking to someone and they’ve ended up talking about a deep and depressing subject which is not really being fun or constructive. There is no harm in asking them an entirely un-related but much more interesting question.

Of course, you’ll need to judge the mood yourself. If they’re talking about a death in the family then you obviously need to be sensitive.

But some clever ways to change the direction of the conversation include:

• Asking a related question but with a different focus – ‘So, what are you gonna do with your time now?’
• Adding your own experience – ‘Hey, can I tell you about the time I did something similar?’
• Changing to a completely different subject – ‘So this is totally unrelated, but…’
• Asking a funny question – ‘Random question for you – noodles or rice?’

Steering the conversation can be a great way to present yourself as an engaging character, and to make a conversation more interesting.

11. Know when to move on

There often comes a point when the conversation is done. Hey, it’s not your fault, it’s just how it is sometimes.

Pay attention to your subject and if they look distracted, or like they need to go, make it easy for them to wrap up.

‘Hey this has been great to chat, but I need to go and do …’

If you’re trying to keep their focus, for example talking to a girl or a business prospect, you can also change direction.

‘Can I get you another drink?’, ‘Shall we dance?’, ‘Can we walk to the next place?’

Or

‘So tell me how we can come to an agreement?’, ‘Do you have a business card?’

Final tips

The best way to make interesting conversation with anyone is to be relaxed and act natural. Let the conversation flow freely, allow for pauses and gaps and have a few anecdotes to hand if needs be.

Avoid drinking to excess, although a beer or two can be a great way to loosen up.

Try not to cut people off, or talk over them. Listen as much as possible, and if you do need to cut them off, ask their permission ‘Can I say something here?’, ‘I must add that…’

Got any tips for making interesting conversation? Share them below in the comments!

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