15 Ways To Date Like A Gentleman

In a world where chivalry and courtship seem to be the stuff of history books, where “Hey, wanna hang out?” via text message is accepted as a date invitation, 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.


The points in this article are not rocket science, they are simply a matter of etiquette, manners, and respect. Qualities that unfortunately have fallen by the wayside. For those of you who hold yourselves to higher standards, how can you ensure that you show the woman you are interested in that you are the gentleman she’s been waiting for?

Make reservations.

A gentleman does not just “wing it” when it comes to a date, particularly early on with a woman he is truly interested in. If you are taking her to dinner, put the forethought into the evening to call the restaurant ahead of time or make your reservations online. Nobody wants to show up on a first date to a restaurant where there is an hour-long wait and need to change plans mid-stream.

Even if you are not going to dinner, the idea here is to plan ahead. Get tickets to the movie, or the show, or the museum, or whatever – beforehand. Be prepared. Show her you are willing to put in effort to actually making sure the two of you enjoy your evening together.

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.

Walk to her door when picking her up.

If you have made the arrangement to pick her up before the date, please do yourself a favor and do not send her a text saying “Here.” or “Outside,” and then wait for her to come out. Get out of that damn car and go up to the door.


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.

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.

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.

Put your napkin in your lap.

It’s basic etiquette, you savage.

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.

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 women are looking for you.

Click here to get my new e-book, The Modern Man’s Guide To Chivalry And Courtship!


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8 thoughts on “15 Ways To Date Like A Gentleman

  1. Is there a LOVE button somewhere??? I am dating the most gentlemanly (is that a word?) man I’ve ever been with. Never lets me touch a door. Makes plans for our dates (asking my opinion of course, but makes plans). Leads through crowds (with his hand back for mine). Waits for me to order and start eating first. Walks closest to the street. Keeps the phone away. Pays for dinner (except for the occasional time when I sneak in my card to pay — learned that from you James!). Always interested in how I’m feeling, what I want to do… willing to change plans if needed.

    Here’s another “chivalrous” thing he does I haven’t seen you mention… he always walks down stairs in front of me and up stairs behind me. Thought is that if the lady slips or falls, he can catch her fall. Kind of dangerous with me because I’m clumsy on stairs but just that fact that he knows that archaic little bit of manners makes him really special to me.

    This morning on the way out of the gym an older guy (old enough to know) let 2 different doors close in my face as I was walking out behind him. I immediately texted my boyfriend and told him how I appreciate the gentleman he is. He stands out from the crowd in my life.

    1. “This morning on the way out of the gym an older guy (old enough to know) let 2 different doors close in my face as I was walking out behind him.”

      Sorry lady, you are NOT entitled to anything from men. Men owe you nothing. Open your own doors.

  2. James as a single middle aged man I have dated many woman. I always follow these guidelines I come by it naturally as my father taught me well. Woman of today sometimes don’t know how to react to a gentleman because there are so few of us. I stumbled across your blog less than 30 days ago but in perfect timing as i met a wonderful woman that I have fallen in love with about that time. Your post on all the subjects you cover are not only insightful but are now my guidepost to being a better gentleman. The woman I’m dating truly appreciates my manners and chivalry. More guys need to read your posts. Keep up the excellent work!

  3. Well written piece! I still had to giggle with the ordering first thing. I’m like Lucy Ricardo (remember the one where she drove the waiter crazy changing her mind?) and also Meg Ryan’s character in the restaurant (not THAT scene) where she is VERY specific on how she wants her meal prepared. It really shows you’re into her when you learn all those quirky nuances about her and can order for her without even asking what she wants. My boyfriend learned to do that with me, and that means anyone can!

  4. Oh man, I’ve made some of these mistakes before (and learned these lessons the hard way! Read about that: http://yinology.org/beyond-my-control/)

    No excuses, bad manners and poor form.

    I’ve also found that women who are not used to chivalry and good manners are taken aback when presented with them. I live in Central Europe (Prague) and the women here are not used to men doing simple things like holding doors open for them. The attitude is changing but the number of times I got odd looks from women because of simple etiquette is quite high.

    Culture is part of the problem, but that shouldn’t mean you should lower your standards.

  5. Hi James, amazing tips, totally loved it! I’m little bit skeptical about the idea on Paying all the bill. What if she insist? what if she really insist? or insist to do 50-50. In my opinion a gentleman should go for the option which keeps his lady happy. What do you think? Anyways Great post and keep up the awesome work 🙂

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