51 Ways To Be A Modern-Day Gentleman in 2021 (Rules & Etiquette)15 min read

It’s no question we live in a digital—always-in-front-of-a-screen—smartphone obsessed society. 

How To Be A Gentleman | GENTLEMAN WITHIN

And with a rise of online dating over the years, it has both men and especially women questioning, “where have all the gentlemen gone?”

Given the name of this blog, I want address my take on being a gentleman in 2021. Think of this as a modern gentleman’s guide to living your best and most courageous life. 

But first, what is the definition of a gentleman? 


According to multiple dictionaries:

plural noun: gentlemen

1. A chivalrous, courteous, or honorable man.
“He behaved like a perfect gentleman”

2. A man who combines gentle birth or rank with chivalrous qualities.
“He’s too much a gentleman to be a scholar”

3. A well-mannered and considerate man with high standards of proper behavior.
“He behaved like a true gentleman.”

4. A polite or formal way of talking to or referring to a man.
“Do you know that gentleman over there?”

If you’d rather listen to this post rather than read it, then I’ve got the audio for you below:


There’s lots of history on what it means to be a gentleman.

To some, it’s defined by a man’s style of dress. Others would say it’s about chivalry; opening doors for a lady or picking up the tab on a date.

Today it means so much more.

Being a modern-day gentleman is about more than dressing the part. And it’s about more than impressing the woman you’re courting.

It’s about compassion and treating others with respect. It’s about doing the little things to make the lives of the people around you easier.

Gentleman Within Manifesto Poster
The I Am A Gentleman Manifesto.

Being a gentleman today is about how a you contribute positively to the world. [Tweet this]

A gentleman has an insatiable thirst for knowledge and education, but an even greater thirst to create and communicate the things he has learned to contribute to a greater good. This is what defines him.

The great thing is that by practicing regularly, it becomes a part of who he is. All that being said, here are my tips on what I feel makes up a modern-day gentleman.


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gentleman quote john locke
“Education begins the gentleman, but reading, good company and reflection must finish him.” –John Locke (one of my favorite gentleman quotes)

1. Say “please” and “thank you,” readily and often

A gentleman can never say ‘please’ and ‘thank you’ enough. These two words are hallmarks of proper etiquette. As a gentleman, it’s beneficial to make a habit of using these two words as often as you can.

thank you please

It’s such a small thing, but this small kindness smooths our interactions and helps other people feel as though you’re aware of them. It’s an essential part of connection, engagement and forward motion.

2. Hand write your thank-you notes

Whether a gentleman is writing to an old friend or his potential boss, a hand-written thank you note can go a long way. Literally no one does this anymore and so this lost art will make you stand out and be memorable to those who matter most.

hand write notes

3. Open and hold the door for others

This one doesn’t only apply to the woman your dating, but to everyone. A gentleman holds doors open for men, women and children alike. Just avoid standing in the middle of the doorway while holding it open, that’s just awkward. 

open doors

A quick rule of thumb, if the other person is relatively far away, don’t make them run. Holding the door in this case is more of a nuisance rather than polite.

4. Alway pay on the first few dates

I understand women today are more and more independent, especially with the meteoric rise of feminism, but consider me old school. I just think it’s the gentlemanly thing to do.

always pay

I almost always expect that a lady will offer to split, and while it’s appreciated I tell her that I’ve got it. If she’s persistent, I say that she can buy us drinks at the next spot.

5. While on a date, keep your phone tucked away

A gentleman knows when it is appropriate and not appropriate to use his phone, whether on a date or not. For a date, my stance is to keep your mobile device tucked away at all times, unless there’s an emergency or you want to show her something that will add value to the conversation.

no phone

6. Tip appropriately and accordingly

Nobody likes a cheap tipper. Many service industries — especially at restaurants — waiters and bussers rely on tips since your generosity is what makes up a majority of their wages. 

tip appropriately

A good rule of thumb is at least 20% at restaurants or service industries like personal care. You can always tip more depending on the service you receive. Just a note: gentlemen always tip well.

7. Speak your mind, but know when to keep quiet

A gentleman speaks up and uses his voice, whether in a meeting or at a gathering with friends or colleagues. What you have to say is important; don’t ever let anyone make you feel or think otherwise.

speak mind keep quiet

A gentleman also knows how to listen to others. When other people are talking, don’t cut them off or try to formulate your response before they’re finished. Intentionally listen to what’s being said and once they are finished then you can say what’s on your mind.

8. Go the extra mile when you know you can

A gentleman knows when it’s time to go above and beyond the call of duty. The beauty of going the extra mile is that that road is often less crowded. And so you’re actually able to go much faster in the pursuit of your dreams, goals or whatever it is that you’re seeking to achieve.

go the extra mile

9. Give your all when you know you have more to give

Whether you’re working on a special project or training for a marathon, you want to give it everything that you’ve got. Leave it all out there. You will almost always be rewarded 10-fold tomorrow for the effort you put in today.

more to give

10. When in doubt, give more

As a gentleman, you always have more to give of yourself. Whether that’s giving more of your time to your nieces and nephews or giving back to those who helped you at some point in the past, you have the power give to others what others once gave to you.

give more

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11. Ask others if they need a helping hand

A gentleman always lends a helping hand, because he knows that when he helps others, he’s actually helping himself. I truly believe that karma exists and that you get what you give in this life.

helping hand

It doesn’t take anything away from you to volunteer or give back to the community via charitable donations. It will always pay to give without the expectation of getting anything in return. 

12. Offer to help a colleague that’s always staying late at the office

Offering to help a colleague if you see him or her always staying late at the office is a small gesture that will not only boost your good karma, but it will earn you a reputation of being a team player.

help a colleague

Be someone who’s willing to give of his time to help a colleague in need. More than likely, they will remember your kind gesture and offer to return the favor someday.

13. Offer your seat to women and the elderly

When you’re out in public on train, bus or subway, make it a point to offer your seat to others who look like they could use it more than you. It’s not only polite, but gentlemanly :).

offer your seat

14. Offers words of encouragement to someone who really needs it

If you see or sense someone is struggling, don’t be afraid to speak up and let them know that you’re there to listen. A little pep talk can go a long way in brightening up someone’s day. 

words of encouragement

15. Know when to take action and do it without being asked

A gentleman knows what needs to be done. If he doesn’t, then he always finds a way to figure it out. Once you find out how, it’s time to get to work. A man who takes action before anything is asked of him, is a man who can excel beyond measure.

what needs to be done

16. Have a firm, but not overbearing handshake

A gentleman has a firm handshake that commands mutual respect. A good handshake is a bit of an art form in itself. Never try to overpower the other person, that just shows a man who tries to assert dominance. Also, a weak/limp handshake is to be avoided too. A firm handshake shows confidence in oneself.

firm handshake

17. Speak clearly and confidently

A gentleman is sharp with his words. He says what he wants to say with precision and purpose. Don’t ever mumble your words or speak so quietly that other people have trouble hearing you. Speak with a voice that commands attention — with strength and vigor. 

speak clearly and confidently

18. Be confident in your abilities

Just as a gentleman should be confident in the way that he speaks, he should also have complete confidence in his abilities and what he has to offer the world.

be confident

If your abilities aren’t where you want them to be, work on it. Perfect practice makes perfect. Whether you’re showing up as a professional athlete or presenting in front of a crowd of thousands, practice, preparedness and purpose is the key. Whatever you do, show up with confidence.

19. Know when to wait your turn and be ready when it is

A gentleman knows how to wait for it. If you’re not making the progress you feel you should be making or that everyone is moving at a faster pace than you are, stop worrying so much.

wait your turn

I’m always reminded that delayed gratification can be one of the most satisfying feelings in the world. A man who can wait his turn will almost always seize the moment when the time comes.

20. Do not disparage the beliefs of others

Not everyone believes the same things. Your God might not be my God while someone else may not even believe in God. We all are entitled to our own beliefs. You don’t have to agree with someone, but you certainly must never disparage the belief of others to make yourself feel better.

beliefs of others

A gentleman respects that all men and women are entitled to their own set of beliefs and that the more empathy we practice, the more room for understanding there will be.

21. Admit when you are wrong

No one is right all the time. And while no one likes being wrong, a gentleman is able to admit when he is wrong, plain and simple. 

admit when you are wrong

22. Do not pick a fight for no reason

There’s a lot of talk these days about dying on one’s hill, believing in something so strongly that you’re willing to die for those set of beliefs. But are you really? That’s the ego getting in the way.

do not pick a fight

If you’re going to pick a fight (not meant in a physical way), then be sure that you’re able to argue the other side as strongly as your own. In life, there are 3 truths — their truth, your truth and the real truth. 

23. Be punctual

There’s a mantra that was ingrained in my brain when I was interning at an advertising agency in NYC back in the summer of 2010 — “to be early is to be on time, to be on time is to be late, to be late is unacceptable, but to stay late is acceptable”.

be punctual

It’s not about being on time, it’s about respecting your own commitments. If you’re chronically late, you’re basically saying that your time is more valuable than those who are waiting for you. Be on time!

24. Live as humbly as possible

A gentleman is a humble man. He knows that there is no merit in braggadocios behavior. He gives credit where credit is due and understands that there is no self-made man.

live humbly

A humble person is someone who doesn’t need constant praise or adulation either. And no matter where a gent is in his life, he knows that he couldn’t have gotten there without some help along the way. 

25. Rise to shake a person’s hand

A gentleman always rises to shake another person’s hand. It doesn’t matter their age or gender, rising to shake hands is a respectful thing to do.

rise up

26. Give compliments sincerely and often

How often do we actually give genuine compliments to other people? Whenever you see something that impresses you about someone else, tell them, they deserve to hear it.

give compliments

Too often we keep our thoughts to ourselves, but a timely and sincere compliment can brighten up someone’s day, and that’s something we could use more of in 2021.

27. Listen intently and be in the moment

A gentleman listens intently to the person speaking to him without passing judgment or formulating his response in advance. He takes it all in, really listens, seeks to understand and responds accordingly.

listen intently

Take a meditative approach to it. While listening to the other person, let your own thoughts go in one ear and out the other. As hard as it is, try not to plan in advance what you want to say. Listen first, respond later.

28. Show initiative and proactivity

A gentleman always steps up. He is the commander of his own ship and knows that if he wants to accomplish great things that he must do all that he can to reach his highest potential.

show initiative

It all starts with a little bit of initiative with a proactive mind-set. Be that go-getter and go get all the things you want out of life from the job to the girl of your dreams. Take initiative!

29. Pay attention to the details

A gentleman always pays attention to the little details. This is being self-aware of himself as well as being aware of what is going on around him. It’s the little things that often go overlooked by most men, but you’re not most men.


30. Go out of your way to ensure those you care about are comfortable

A gentleman is sensitive to the feelings of those around him, especially those he cares deeply for. Whether his parent, niece, nephew or significant other, a gentleman always asks how they are doing and what he can do to make them feel more comfortable.

31. Try to keep swearing to a minimum

A gentleman watches his mouth. Swearing is okay for emphasis, but swearing like a sailor — F word this, F word that — is not the way a gentleman behaves.

32. Try your best not to judge

It’s impossible not to judge others, it’s in our human nature to do so; however, a gentleman is aware of this and tries his best to be non-judgmental. No one likes that feeling so it’s best to treat others the way we want to be treated.

33. Encourage others

A gentleman encourages others when they are feeling down. He sees potential in others, he pushes them to be their best selves, to strive for greatness.

34. Embrace change

Change is the only constant. A gentleman knows how to embrace and adapt to an ever changing world around him. Never get too comfortable with any situation because a change is gonna come.

35. Demonstrate personal responsibility

A gentleman is responsible for his behavior and actions. When he does something wrong, he owns up to it. He knows what his responsibilities are and acts in accordance to what he must do.

36. Provide for your family

A man and a gentleman always provides for his family. If you have a wife and kids, they will depend on you to step up and be the man of the house. Simply put, a man provides, no matter the circumstance.

37. Have respect for others and their privacy

A gentleman always respects other people even if he may disagree with them. And he certainly does not infringe on others’ personal space. Others’ private matters are none of his concern.

38. Get up, dress up and show up

Life isn’t always easy. Some days we don’t feel like getting out of bed to face whatever harsh realities we’ve got to deal with. But a gentleman rises up, gets dressed and shows up no matter what. 

39. Provide more in use value than you receive in cash value

Though it’s hard to measure how much use value you’re providing, just know that in life, you are rewarded in cash value for the things you provide in use value.

The key is to overwhelmingly add as much value as you possibly can, the money will follow. A gentleman knows this and works accordingly.

40. Help a stranger move her trapped vehicle out of the snow

This includes small gestures of kindness that might not take much from you, but will mean a whole lot to the person you’re helping. A gentleman sees when someone might be in trouble and does what he can to help at a moment’s notice.

41. Talk less, smile more

Shoutout to Aaron Burr from the Hamilton Musical, but this one is a gem. A gentleman doesn’t show all his cards. Let others talk about their grand plans. Sharing too much can wind up biting you in the foot. Sometimes all you need to do is smile and have a positive attitude. 

42. Learn to tie a tie

Here are the classics to be familiar with:

  • Windsor knot
  • Half-Windsor knot
  • Four-in-Hand knot
  • Pratt knot
  • Bowtie

Tying a tie is relatively easy and once you learn how, you’ll never forget, like riding a bike.

43. Learn how to politely leave a conversation

Have you ever been in a talking to someone at a party or conference and you can feel the conversation coming to an end? Or maybe they’re talking non-stop and you need a breather.

Be upfront yet respectful and let them know that you want to go and say hi to some of the other people in attendance. Exchange contact information if it makes sense to do so.

Alternatively, if you’re speaking to more than one person, you can say to the group that you’re going to run to the bathroom or grab a drink. It’s an easy, frictionless way to slide out.

44. Be a man of your word

A gentleman keeps his word. He says what he is going to do and then he does it. Your word is your bond and so it’s important to stay true to what you say you’re going to do.

45. Keep toilet paper stocked at all times

You never know when the next pandemic will hit and the rest of society will go on a frenzied trip to the grocery store to completely wipe out the toilet paper aisle.

Kidding aside, it’s always helpful to have a bathroom full of essentials, including toilet paper rolls, just in case someone needs it in a pinch. Just saying!

46. Seek to make life easier for others

A gentleman’s job is to make life easier for those around him. First, take care of yourself, because if you don’t have your own life together, you can’t serve others to the best of your abilities.

Then go out of your way to help your family, friends and the people around you. Be of service, give of yourself, your time and ask yourself if what you are doing is helping rather than harming.

47. Speak up and stand up for those who can’t

Not everyone is willing to stand up for themselves. A gentleman sees this and is the first to speak up and stand up for those whose voices are silenced, especially if he has the platform to do so.

48. Be dependable

A gentleman is someone who can be relied upon. Others will look to you to provide, to serve, to step up to the plate. This also means that you keep your word and do what you say you are going to do. 

49. Be loyal to those who have provided for you

Loyalty is having strong support for those who matter most in your life. A gentleman is loyal to those who have provided for him during his upbringing. 

Not everyone is lucky to have a strong support system, but if you did have one growing up, always remember to stand by their side when they need you most.

50. Have an open mind 

An open mind is a mind prime for growth. You will not always agree with your family, friends or co-workers, but be open to trying a new approach or something you haven’t experienced before.

A gentleman always has a growth mindset and is ready and willing to hear any and all options in front of him before making a decision.

51. Dress for the occasion

When you dress the part, the people around you notice. A gentleman always dresses for the occasion. It’s a hallmark of what I consider timeless style.

Have an interview? Going on a date? Hosting a gathering of colleagues? Whatever you’re doing, wherever you’re going, it will benefit you to dress appropriately for the situation and occasion. 

And there you have it, my long list on how to be a gentleman in 2021.


I’m not quite sure where they all went, but what I do know is that in 2021 and beyond, it is the men who are striving to be more gentlemanly in the way that they behave, dress and ultimately live their lives are going to have a leg up on the competition.

On Being A Gentleman | GENTLEMAN WITHIN


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In summary, the characteristics of a gentleman can be defined as being:

  • Noble
  • Loyal
  • Generous
  • Chivalrous
  • Educated
  • Self-aware
  • Adaptable
  • Responsible
  • Empathetic
  • Respectful
  • Dependable
  • Courageous
  • Well-dressed


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In the end, no one can be a gentleman 100% of the time, but striving to be one is courageous and always worth it. The beauty in striving to be a modern-day gentleman is that the more conscious you are of it, the more apt you will be to practice it in your everyday life. 

It’s not always easy, but keep pushing to be the best man—gentleman—that you can be, not just for your own well-being, but for a world that’s hopelessly in need of it.

This article was originally published on Sept. 26, 2016. It has since been updated for comprehensiveness.

How To Be A Gentleman | GENTLEMAN WITHIN

What do you feel makes up a modern-day gentleman?

Let’s continue the discussion over in the Gentlemen Within Private Facebook Community.

Looking forward to seeing you in there.


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  • 564


  1. Susan Winter says

    Love your commentary. Thank you for this wonderful podcast!

  2. Keith Mccall says

    This is great! I love the content of the blog very informative.

  3. Kevin Shahroozi says

    I think what also makes a modern is dressing sharp and dapper in this age of many millennials wearing sweatpants and oversize hoodies on a date with a beautifully dressed woman.

  4. Khoi | Gentleman Within says

    Hey Kevin, I can agree with that. It’s never a bad idea to dress it up for a date, especially a woman of taste.

  5. Adam O'Shaughnessy says

    Thanks so much for reminding me with this excellent list Khoi. So very well stated. None of us is perfect, but regardless of where we come from in this world we must strive to think of the needs of others, especially those less fortunate. We must have values and courage in the face of adversity even though it can be and often is difficult. One learns to be better over the course of many years. Our conscience teaches us when we know we can be true to what is right. How we dress and present ourselves – our manners – are of course important. Courage, tenacity and strength of will are important. But compassion and caring is the most important part of the chevalier, the gentleman.

    • Khoi | Gentleman Within says


      Thanks for leaving this thoughtful comment. I agree completely! We’re all a work in progress and I think we should be kind to ourselves as we strive for betterment every day.


  6. Tim Sabat says

    Amazing list. It’s useful when I forget that being a man is not only one value.

  7. Richard Hanson says

    Just discovered the blog. Really looking forward to looking around. Thanks for taking the time to pour into men’s lives.

    • Khoi | Gentleman Within says

      So glad that you found the blog! And thanks for taking the time to leave a comment. If you have any questions, don’t hesitate to ask!


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