12 Tips for Being a Modern Gentleman

I’d like to dedicate this article to my mother. Since the age of 8, my mom would stand in front of a door until I opened it for her. She aspired to raise me as a gentleman, just like her father, my namesake, was.

This article doesn’t simply go through the boring basics of chivalry — it strives to go deeper. There are reasons behind the rules. And then there are ways of thinking about being a gentleman that simply go beyond rules.

You’ll notice most of these tips are “gendered,” but I think they can apply to any situation in which one person wants to make someone else feel taken care of — which is the simple goal of all gentlemen.

But, if you still find some of this sexist, you can take it up with my mom.

1) If You Do Nothing Else, Just Keep Your Radar Up. Gentlemen have a sixth sense. They recognize situations that may require them to swoop in and save the day. That woman with the baby stroller? She might need a door held. That man with the walker? He might need a hand navigating those steps. You’re thirsty waiting for dinner to come? Then it’s likely everyone else at your table is too.

As gentlemen (and women), we strive to make others feel taken care of. Keep that in mind, use common sense, and you probably won’t need to remember any silly rules — although some of the rules may surprise you.

2) Run Toward the Fire. Another way of saying this is Never Fall Prey to the Bystander EffectThe Bystander Effect is a psychological phenomenon in which people will not offer help to someone in need when others are around. Multiple people have died and entire buildings have burned to the ground because those who saw the first signs of violence or the first wafts of smoke failed to call the police. They assumed someone else would help.

These are extreme cases, but the Bystander Effect happens everyday in small ways. The woman who gets harassed on the subway while no one says a thing. The old man who fumbles with his groceries getting in the door to his building as people walk past him. The tourists staring confusedly down at a map while everyone around them has a smartphone with a local data plan in their pocket.

Stop. And. Help. Them.

3) Let Others Enter, Sit, and Eat First. There’s really nothing worse than watching someone over the age of 12 selfishly reach for food and serve themselves first. Or watching young people of apparent good health rush onto a subway car and sit down before the slow moving elderly. It’s just such a let down, and so easy to fix. So, be the guy or girl who serves others first — no matter how hangry or in a hurry you are. Be the one who let’s others ramble up the subway steps before you. Or merge into traffic in front of you.

It’s such an easy little thing that makes everyone smile.

EXCEPTIONS: There are a few important exceptions to this rule:

  • When entering a dark or unknown space, chivalry dictates that the man should enter first to make sure it is safe for his lady to enter.
  • Going up stairs, a gentleman goes first, so his lady’s rear is not embarrassingly on display right in front of his face. Exception to the exception: If the stairs are treacherous and she’s in inconvenient footwear (per usual), it might be best for you to spot her. Talk about it.
  • Getting in a cab, if there’s no option to walk around after you let your date get in first, explain that you’ll get in first so she doesn’t have to slide, and then jump in ahead of her.

4) Call Women You Don’t Know “Miss” or “Ma’am” Until They Tell You Otherwise. The age of using pet names with women you don’t know is long over. While some women will still call you “love,” “sweetie,” or “doll” (especially those working in hospitality) you don’t get to do the same until you have established some level of familiarity.

My rule of thumb on choosing between Miss and Ma’am is: If she’s old enough to be my mother, or if I KNOW she’s someone’s mother, I go with Ma’am. Although calling a woman who could be my grandmother “miss” or addressing a pair of elderly women as “ladies” or even “girls” normally gets a warm giggle.

5) Walk on the Proper Side of Your Date. Back in the days of horses and open sewers, the street side of the sidewalk was the smelly, dirty, and sometimes dangerous side. As such, a man would walk between the street and his lady to protect her from the stench, refuse, and potential to get splashed that lived just beyond the curb.

These days, you could say we still walk on the street-side to protect a lady from puddles and errant bike messengers. No matter what the motivation, it’s a great touch that makes a woman (or anyone, really) feel taken care of.

A few things to keep in mind:

  • When you switch sides of the street, slow your pace, step behind her, and gently move her across in front of you. It should feel smooth, not forced. If you’re zig-zagging through the city and switching sides all the time, you might choose a simpler path that has fewer turns.
  • When Indoors, Walk with your Date on Your Left SideThis tradition arises from medieval times when a man had to keep his “sword (right) hand” free in case of danger. In modern military tradition the rule still applies, so a man’s right hand is free to salute. But even if you don’t have a sword or the need to salute, it’s just the classy thing to do.
  • EXCEPTION: This entire tradition goes out the door if your date insists on wearing her purse on a particular side, as her purse should always be on the outside — except in dodgy neighborhoods when you should keep it between you. In either case, just roll with it. As I said above, this is all about making others feel more comfortable, not rigidly adhering to the rules.

6) Wait Till Your Date or Friends are Inside Before Pulling Away. You wait so you know they are safely inside the house. It takes 10–15 extra seconds, but is remembered forever. And you really would never be able to live with yourself if you just sped off and something happened.

7) Ask Your Date What She Would Like, and Order For the Two of You.This may ruffle the feathers of some, but I’ve never had anything but good feedback when doing it myself. It normally goes something like this:

Me (to my date): What looks good to you?

Her: The duck sounds amazing.

Waiter (addressing both): Are you ready?

Me (to the waiter): Yes. The lady will have the Duck, and I’ll have the Filet. And we’ll have a bottle of…

If she has ordered something that requires more information like sides or a temperature, the waiter will normally ask her directly.

Bonus Points: Order a wine that best pairs with her meal.

8) Offer Your Umbrella to the Elderly or to Women with Children.Holding the umbrella for your date is common sense, but holding it for strangers is a true show of chivalry.

If you think about it, there are few situations in which you should be walking under an umbrella alone on a crowded street. There is almost always some poor soul getting drenched while you delight in your preparedness. I’ve walked dozens of elderly ladies and women with small kids a block or two out of my way in a rain storm, often giving them the umbrella at the end. It’s just the right thing to do.

You can also offer an umbrella to a woman closer to your age, but that comes with an overtone of romantic interest you should defuse immediately if it is not intended or just be pretty damn charming if it is.

9) Learn How to Change a Tire, etc. There are few things less attractive to a woman than her man not having basic physical competencies like changing tires and fixing small things. What’s more, it’s just plain irresponsible and dangerous. What if you’re out of cell range and can’t call AAA? What if they can’t come for 4 hours?

If you’ve never done it before, or if you honestly have no idea where the jack and spare are in your car, figure it out TODAY. There are dozens of online tutorials on how to change a tire, and your car manual has info on where to find the tools.

Be the Hero — Change the tire.

10) Send Flowers and Thank You Notes. There are few situations in which sending flowers or a thank you note is a bad idea.

To do flowers right, you first need to find out what flowers she likes. Not everyone likes roses. In fact, only one woman I’ve dated said she liked red roses. “They are so cliché.” If you don’t know what she likes, tulips, irises, or even a live orchid show a little more originality than roses.

That said, you don’t need to overdo it. Sending five dozen long-stem roses out of nowhere stinks of insecurity and desperation. A simple bouquet of what she likes with a short note is perfect.

As for Thank You Notes, they are an appropriate response to any display of generosity. Were you a guest in someone’s home? Thank You Note. Did you get a surprise gift from a friend? Thank You Note. Did a colleague send you new business out of the blue? Thank You Note.

Just do it. My Mom would be proud.

11) Open Doors — Properly and For Everyone. I hold doors open for everyone. Women, men, pets… Again, it’s something my mother taught me. But there is a right way and a wrong way to do it.

  • If the door opens towards you, open the door, stand aside, and let the other person walk in front of you. Opening, walking through, and then leaning back and holding it awkwardly while halfway in the doorway simply doesn’t work.
  • If the door opens away from you, walk through the door, and hold it open until the person comes through. Opening the door awkwardly while still in the doorway and making the person slide by you just makes everyone uncomfortable.
  • If you are driving, before you get in, unlock the passenger side door and open it for whomever is riding with you — even though you have a key fob — even for friends of the same sex. It’s just polite. But when you arrive, jumping out and opening the door for your passenger is optional depending on your relationship and the context.
  • If you’re getting in a cab, hold the door for other passengers and then walk around. Don’t make people slide across the seat unless you are on super familiar terms. But never make a woman in a dress or heels slide over, no matter what.

12) Dress for the Occasion. Entire volumes have been written on this topic, so I will be brief. When invited to someone’s special party, scan the invitation for a dress code, and then stick to it. Contrary to you thinking you’re “not a suit guy,” it is a terrible display of disrespect to show up to a semi-formal wedding in slacks and a button down. If you don’t own a suit, buy one. I provide more advice on the topic in another article here.

There are a million other rules I could harp on, but these are the big ones. If you feel I missed something crucial, please let me know.