5 Conversation Starters Every Gentleman Keeps Handy

The art of conversation... It can be a tricky one to properly execute.

As a gentleman, you'd never runs out of things to say.

This usually means being the life of the party. So keep your best stories handy ;)

A gentleman also never attends an event and lays low in a corner, hoping nobody sees him.

There's nothing charming about that.

Though carrying a conversation isn't always easy, when you're well equipped it's never an issue.


In my early 20's I knew getting this part of my life figured out was a key to succeeding personally and professionally.

It always seemed that the men who were dating the cutest girls and had the coolest jobs were the smoothest talkers.

Something I wasn't back in those days.

Growing tired of having low self esteem and not being able to work up the courage to strike up conversations with anybody, I knew something had to change.

So I dove in the deep end...

Getting a serving job was the solution!

This meant that I was forced to talk to people or fail miserably at my new job (which wasn't an option).

You literally can't succeed without talking to people, even if your conversations are lacklustre at best.

Don't get me wrong, early on the number of awkward conversations I had far outnumbered the charming ones.

Eventually that turned around.

Reading How To Win Friends And Influence People was a key to that success.

But the biggest factor was actually getting in the reps and stepping out of my comfort zone EVERY SINGLE DAY.

During those years I discovered what actually made for great conversation and how you can easily start a conversation without hearing crickets.

Before we dive into that, it's important that I share with you $20,000 lesson.

Disclaimer: that was basically the cost of tuition for four years of university ;)

In all seriousness, one of the best conversation tips I learned was back in journalism school.

That tip is to ask open-ended questions.

This leaves room for people to expand on what you're curious about which can only encourage the conversation to keep growing.

Closed-ended questions typically lead to one word answers like 'yes' or 'no' and 'good' or 'bad.'

Not exactly the most energetic approach since it can be tiring for everyone involved.

This also doesn't allow you to extract more information from the person which would lead to new angles within that conversation.

Today I'm going to share with you the 5 Conversation Starters Every Gentleman Keeps Handy


 1) When In Doubt, Start With A Compliment

We all love a good compliment!

It's a great way to boost your confidence and can instantly make you like the person offering it.

Assuming that it's genuine.

Pay close attention to how they're presenting themselves.

Offer a compliment that's authentic and isn't just a generic remark that you could say to anyone and everyone.

Don't gamble with anything less than a genuine compliment no matter how charming you think you might be.

People can ALWAYS sense when you're forcing it.


2) Be Aware Of Your Surroundings, Make An Observation

Pay close attention to what's going on around you.

It's one of the many secrets of how a gentleman strikes up a conversation.

Not only will get your conversation going, it's also a neutral topic that nearly everyone feels good talking about.

As a gentleman, your goal is to make people feel comfortable and willing to engage with you.

It's a great way to get them to open up.

This can be especially handy if your goal is to ultimately ask them for something - like out on a date or to schedule a meeting in the near future.


3) Ask Them About The Venue/Event You're Attending

This is a great way to get the ball rolling.

It works especially well in places like restaurants and coffee shops - specifically ones you've never tried before.

Not only do gentlemen use this to strike up a conversation but it's also a great way to gain information, like a recommendation for what to try.

Maybe the place you're visiting is well known for a specific dish or drink which you never would've discovered without striking up a conversation.

4) Feeling Bold? Try Cracking A Joke To Break The Ice

Tread lightly with this one.

The secret to executing it properly (without offending or looking bad) is ALL in the delivery.

The content of the joke isn't nearly as relevant. Obviously you'll want to  avoid anything political, sexist, or racist.

One of the best feelings you can give a person is making them smile.

A gentleman knows that doing so will ALWAYS leave a memorable impression with them for all of the right reasons.

Do your homework and be prepared with a list of 3 to 5 go-to jokes that you keep handy.

Before taking the leap in front of a cold audience, make sure to test them with your inner-circle of friends and family.

This way, you're less likely to burn any bridges since they already know you.


5) As A Last Ditch Effort, Talk About Current Events Or Seasonal Activities

I say 'last ditch effort' because this one can lead to a generic conversation.

Current events are often what you talk to your co-workers about during the elevator ride up to the office.

This approach does have its benefits though.

It's typically based on something most people would be up to speed on, like playoff hockey or basketball.

Consider this angle your foot in the door.

Especially when chatting with someone you're not too familiar with. It's a great way to get them warmed up to you.

Remember that when you're making a first impression that up to 90% of what the other person's thinking is "what are your intentions towards me?" 

Last Thoughts:

That should be more than enough to get you striking up conversations with anybody.

Being a natural conversationalist is another trait that all gentlemen possess.

Just be careful of falling into the trap of making small talk.

It's easy to do because anyone and everyone can carry it on with little to no risk of offending.

I hope you enjoyed reading this as much as I enjoyed writing it.

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