The Gentleman’s Guide To Dating: How To Be a Man in a Sea of Boys


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

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?


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 finding the mate. The strongest gorilla passing his genes to the next generation. The strongest lion leading 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.

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.

Do not start eating.

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

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 judgement if you surround yourself with idiots.


Be punctual.

If you are picking her up at 7:00, be there at 7:00. 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.

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 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.

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.

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.

Keep your cell phone away at all times.

Unless you are an on-call doctor or Barack Obama, your emails can wait.


Pay for dinner.

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

Open all of the doors for her.

All of them.

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.

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.

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.

Put your napkin in your lap.

It’s basic etiquette, you savage.


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.

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. 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, 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.


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22 thoughts on “The Gentleman’s Guide To Dating: How To Be a Man in a Sea of Boys

  1. @ Kevin, you are entitled to yr opinion. What you are not entitled is to crash other people’s parties and insult. Don’t like it, don’t eat it. And if you don’t have a nice thing to say, say nothing at all. Go away. You are just plain rude.

  2. Very well put. I am often slightly amused when I hear men complain and not realize that just having some basic manners will go a long way. I also feel it is the responsibility of those of us that are adults to lead by example for the boys around us that are just learning about this thing called dating. I appreciate your writing.

  3. Well… Manners are what make us successfully work as a society. Without them, it is chaos. And having good manners just translates into showing respect. What possibly could be wrong with that? So I find it strange when people (both boys and girls) call it outdated. Outdated? Why? Because their parents didn’t teach them or because they weren’t able to retain the knowledge? Or because, no matter how intelligent they are, they choose to keep being ignorant?

  4. HA he deleted my comment. I am just stating the fact. He is offering people dating advice when he has nothing to show for it himself. Just an oxymoron in my opinion.

    • Hi Kevin,

      I notice that this is the 2nd time you’ve commented from the same IP address in Waltham, but under a different name, so forgive me if Kevin is not proper to call you…

      Anyway, I am curious about the sources of your claims. The company I was working with full time previously is crumbling underneath itself, and I have chosen to be single because my previous relationship wasn’t what I wanted in the long term – I think this is fair, and frankly I’m not quite sure how it plays into my right to have a personal blog where I write my opinions down.

      Care to elaborate a little bit on the connection, and how the *reality* of my life circumstances (not that they’re your business), match up with your previous claims?

      By the way, thanks for visiting my site repeatedly and helping my rankings!

      – James

  5. He is a quack. Posing as an expert when he is not. A similar scenario is a person that gives out medical advice but is not a doctor. Its not safe. He will probably have a lawsuit on his hands if he continues to give “advice” to unsuspecting audiences.

    • Oh and one other thing, “Kevin,” I am assuming you and I know each other in person since we are from the same area and you clearly like to make personal comments about me – this wouldn’t make any sense if you didn’t know me. So, I just want to apologize for whatever I may have done to you on a personal level to cause you to have this kind of animosity against me. I am happy to talk it out in person if you’d like.

      Let me know.

      – James

  6. @ Kevin, I don’t care if he’s lucky at love. He’s not ”offering people dating advice”. He’s offering people GOOD advice (as in opposite to bad advice).
    There will always be women who prefer to be mistreated or think that they are happy with a partner that won’t consider them as such. That’s their choice. But intelligent people (women included) know they should treasure those who respect them and will show them back the same.
    If Mr. Sama hasn’t yet found a partner who treasures him that’s not an issue here. I’m pretty sure he wouldn’t be happy with a partner who wouldn’t appreciate a gentleman.
    Standards, Kevin, standards.

    • he calls himself a dating coach… where are your credentials?? you are not certified in any way. opinions are not advice.

      • Welcome back, Kevin! I noticed you ignored my direct comments and questions to you regarding what I may have done personally to you for you to be so agitated. Would like to know how I could make it right.

        Also, no credentials are required to have a personal blog. Thanks again for the added traffic to my site!

        – James

  7. I really don’t see how anyone can find this post or other similar posts offensive. Attacking the speaker personally just shows a lack of maturity on the part of the attacker. As others have stated, this is basically all common sense but sadly that has become quite rare these days.

  8. James, the world needs this – keep writing! And I promise to keep reading. Thanks for the thoughtful and fresh take on what it means to be a real man in today’s world. 🙂

  9. James, thanks for another good blog. Respect is certainly lacking in the dating world. I look forward to reading your blogs. You are stating your opinion and don’t claim to be a relationship expert specializing in therapy so I don’t see your being sued as an issue. Many of us support you and those who don’t like what you have to say can simply stop reading your blog. There’s no need for personal attacks. Kindness and respect will accomplish so much than displaying disrespect. I wish you well James!

  10. This article is very good and a must-read. Guys would do well to practice these tops even when just out with friends, or at work. Every social situation requires manners after all. Kudos!

  11. James, I think you have the best dating/relationship/treatingothersasyouwouldwanttobetreated advice I’ve read by far. I’ve literally had so many bad encounters in dating and relationships that I have a phobia about dating now. When I come to your site and read your posts it helps restore my faith in humanity.

    Evan Marc Katz has nothing on you. His advice is practical but unsympathetic and he attacks his female writers and gives a slap on the wrist to his male writers while still directing the blame toward women. You mainly give advice to men and that’s the missing equation in all of these dating blogs. I do wonder though how many men actually read these blogs, it would be an interesting statistic to find out. I do wish there was a better way to reach men, us women can’t make the change happen without them.

    When I need to restore my faith in love… and men I read your blog as well as Good Men Project (which I’ve seen your advice featured on). Keep up the great work James. We need more role models in society like you (regardless if you are single or taken).

  12. Dear James-

    There is one occasion that a man walks on the inside of the sidewalk – in old days New Orleans in the French Quarter, “Ladies of the Evening” would hang out windows and hassle the ladies on the sidewalk. Therefore in the French Quarter, it was proper for the gentleman to protect his date from these hussies!

    I enjoy your blog.

  13. Pingback: The Gentleman’s Guide To Dating: How To Be A Man In A Sea of Boys – Beautiful Articles

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