17 Rare Ways To Stand Out As A Gentleman In A Sea Of Boys

Let's prove chivalry isn't dead.

man smiling Bricolage/ Shutterstock

In a world where chivalry and courtship seem to be the stuff of history books, and men complain that they shouldn’t have to pay for dinner if women want equality — it is plain to see that we need to bring some dignity back to dating and relationships.

My belief is that there are so many mixed messages about what women want in a relationship, that we, as guys, can easily get confused. Does she want her independence? Does she want to be courted? Will she be offended if you pick up the whole bill? But then if you don’t, you never get that second date. What gives?


The truth is that the basic fundamentals of courtship have remained the same over time. The idea is to set yourself apart by showing a woman you know how to be a gentleman, that you are genuinely interested in her, and that you are willing to put in the consistent effort — not just during the first few dates, but over time (potentially forever).

RELATED: If A Guy Does These 5 Things, He's Trying To Keep You Trapped In A Toxic Relationship

If this sounds like a lot of work to you, consider this: A woman who loves and cares for you will always exceed or match your efforts. Teamwork makes the dream work. It is far more fulfilling to put effort into one relationship with a woman you truly love than it is to put effort into always meeting a new woman a few months later because you didn’t give someone the attention she deserved.


As a gentleman in the modern era, you immediately set yourself apart by how you carry yourself, how you present yourself, and how you treat others. Being a gentleman is nothing more than holding higher standards for yourself than most of the population; this is why being a male is a matter of birth, being a man is a matter of age, but being a gentleman is a matter of choice.

But let’s cut to the chase. What can you do, realistically, in today’s dating world to attract a mature woman who is tired of playing games? Here's how to be a gentleman and keep a woman interested in you, whether it's a first date or a relationship.

Here are 17 rare ways to stand out as a gentleman in a sea of boys:

1. Stay humble

Yes, evolution and biology tell us that the biggest, baddest dog in the yard gets the girl. Hence, the brightest-colored male birds find their mate. The strongest gorilla passes his genes to the next generation. The strongest lion leads the pride.

But what is necessary to the evolution of our species (and therefore attractive) is evolving, itself. Women who make their own money and have their own possessions are not impressed by yours. Sure, she will want to know you are ambitious and can match her efforts in life, but bragging about who you’ve met or what you drive, or where you live, will send her running for the hills.


Remember: If you’re good at something, you’ll tell everyone. But if you’re great, everyone will tell you.

RELATED: 5 Little Tricks To Make Him Choose You Over Her

2. Quit swearing

Alright, I can swear like a drunken sailor with the best of them, but there is a time and place for everything. In the presence of a lady in a dating scenario, try to clean it up a little bit.

It’s one thing when you’ve become comfortable enough with each other to take off the filter, but for Pete’s sake, man, censor yourself at first.

3. Do not start eating

Unless her food has come out, too. Remember, ladies first.

4. Do not talk badly about others

There is nothing attractive about someone who has to make others look bad in order to make himself look better. If you are complaining about the people in your life, your date will begin to wonder what type of negative things you may say about her when she’s not around.


Also, it shows poor judgment if you surround yourself with idiots.

5. Be punctual

If you are picking her up at 7 PM, be there at 7 PM. It’s not just a matter of being on time, it’s a matter of showing her early on that you stand by what you say, are reliable, and trustworthy.

6. Stand up and greet her if you are meeting her somewhere

I personally would much rather pick a woman up for a date and have never had someone suggest that we meet somewhere because she was uncomfortable with me knowing her address, but I understand in the age of online dating sometimes this trust is a little harder to come by.

For this reason, some women who are tired of playing games may insist you meet at your destination. If this is the case, arrive first (never keep a lady waiting), and stand to greet her when she does arrive.


RELATED: 12 Signs He's Not In Love With You — He's Obsessed

7. Maintain eye contact.

Don’t break a sweat doing your best not to blink and to stare into her eyes all night long... that would just be weird. But spending the evening staring at your shoes or the tablecloth is a great way to show your date that you haven’t quite mustered up the self-confidence to have an adult conversation with her.

I understand it can be nerve-wracking to get to know someone new, particularly in a one-on-one situation. But when your nerves begin to get to you, remember that she is out with you because she is interested in you as well. Good eye contact is important, particularly when listening to her. It lets her know you’re paying attention.

8. Be kind to everyone

I have always said that a person who is not nice to the waiter, waitress, or bartender is not really a nice person. They can get everything right with how they treat you, but if they are rude to people they’re not trying to impress, this is a big red flag.


A gentleman is not kind to others because of who they are, he is kind to others because of who he is.

9. Keep your cell phone away at all times

Unless you are an on-call doctor or the president, your emails can wait.

10. Pay for dinner

All of it. The whole bill. The entire thing. It’s not about the money, it’s about the gesture.

11. Open all of the doors for her

All of them.

RELATED: 15 Signs Mr. Right Is Actually A F-Boy In Disguise

12. Understand who leads and who follows

When being seated at a restaurant, allow her to go first and follow behind the host or hostess. When walking through a more crowded place, though, you lead and help clear the path for her.


For an added bit of charm, casually extend your hand behind you for her to hold onto. If she takes it while following you, take this as a good sign.

13. When ordering, she goes first

The ultra old-fashioned still sometimes prefer to find out what their date would like and then order it for her, but to be safe, your best bet is to simply have her order first when the waiter or waitress arrives.

14. When walking together, you walk closest to the street

The purpose of this lost art is to show your willingness to be splashed instead of a woman should a passing car run through a puddle.

Furthermore, in some countries, people would throw trash out of windows, and the person walking closer to the building was less likely to be hit. It’s an effortless way to show her that you care, and are willing to protect her.


15. Put your napkin on your lap

It’s basic etiquette, you savage.

16. Do not have an "end goal" for the date

If your intentions for the evening are to take this woman home at the end of the night or something of the sort, she will be able to see right through you the entire time. This is a great way to ensure never getting a second date with her.

It is important to understand that if you are out with the right woman, there is no goal or final objective to be pursued with her. Time with her is the goal.


Sharing an evening with her is the objective. Your time together is the entire point, therefore there is no “end” to work towards because if you do things right, you will be seeing her again soon anyway.

17. Always gauge her comfort level and act accordingly

Perhaps one of the more difficult but valuable things for men to do is to learn to read women, especially those who are tired of playing games. Picking up on non-verbal cues, body language, and subtle facial expressions can change the entire course of your evening. It will tell you if you should or shouldn’t go for the kiss, should or shouldn’t suggest you go somewhere else after dinner, and should or shouldn’t invite her back to your place for a drink.

Non-verbal communication is a very important piece of the puzzle. You will have far better chances with a woman if you can see she is tired or not feeling well and go home, than if you were to just hang around and overstay your welcome.

Patience is an important tool in any gentleman’s arsenal. Never rush her, never make her feel pressured, and never force yourself on her in any way.


Unfortunately, these simple guidelines are overlooked more often than not in today’s society. But the good news is, as a gentleman, it is easy to separate yourself from the crowd by putting in just a little bit more effort.

It will be appreciated, gentlemen, because the frustrated women of today are looking for you.

RELATED: If Your Guy Does These 16 Things, Congrats! He's A True Gentleman

James Michael Sama is a relationship expert who writes about dating and relationships. He speaks on the topics of chivalry, romance, and happiness, and has been featured in news segments, talk shows, and mainstream radio.