The New Rules
of Chivalry

The New Rules of Chivalry

The modern man’s guide to being a gentleman in the digital age

Digital relationships in 2020

Chivalry ... you’ve heard it’s dead. You’ve heard it isn’t. Me? I like the concept. It's brave yet humble; kind and aware of what to fight for. But it isn't timeless. It gets its definition from knights in medieval times—more than 500 years ago. And there are “gentleman norms” from 50 years ago that are, to say the least, out of touch. But rather than declare it dead or alive, let's adapt it to modern times. Times in which most of our interactions happen virtually.

Call it eChivalry. By now, you're aware you have both a physical life and a digital life. Now more than ever, you make first impressions via digital communication and tend to an electronic reputation. You even have a digital visual aesthetic and tone of voice. Whether you're swiping right or sending resumes, the best way to stand out is by being a virtual gentleman. Here are the new rules.


Learn a new way
to listen

Think of this as the new, “Look a man in the eyes when he's talking to you, son.” Which means simply show the other person you're listening to them. The same rules apply for video chats, but how do you listen to a text? Or email? Maybe you're rolling your eyes. You read them, duh. But it's not always that easy. This morning, I got a text. I unlocked my phone and right as I did so, I got an Instagram ping. So I opened that and maybe an hour later I closed out of YouTube wondering why I had picked up my phone in the first place. This is the biggest difference between listening digitally and listening IRL. Be intentional when you're checking your inbox or DMs. Read a message as if you're sitting across the table from that person.

Be good.
Not perfect.

The benefit of electronic communication is that you do have time to think about how you reply. But that doesn't mean you should torture yourself. Here's a tip (pardon the rhyme): Write it square, then write it with flair. If you're trying to say, “Nice to meet you,” in an email, put that at the top of the page. Below it, write it a different way. “Pleased to extend a digital hand.” Rinse and repeat. This will help you stand out by saying things in a unique way.

Digital first impression illustration

Make your
first impression memorable.
Not shocking.

Most dating app threads begin with “What's up?” or something equally worthy of a yawn. You may as well open with “Hi, I'm a bowl of plain oatmeal.” Don't be that guy. You're more interesting than that. Opposite of “What's up?” is a more unfortunate option—some outrageous statement that's only value is shock. This is the tactic of trolls. Those who are too afraid to be themselves.

Luke Sullivan, professor and author, once described it as someone walking into a room full of people, spitting on the floor, and leaving. Memorable? Sure. Enjoyable? Not for anyone. Just be honest with your introductory remarks. What's on your mind today? Why are you even typing the message? Start there. For instance, if I were sending a message right now, I may say that I'm a writer, working on a piece about how to be a virtual gentleman, and ask if they want to help. In a professional setting, include something personal that's relevant. And get it to two sentences.

Look good without
looking like an influencer

You don't need to feel ashamed for wanting to look good on a video chat. We cringe at the thought because we've all seen influencers in the wild with their ring lights. But there are small things you can do to show you're making an effort—both personally and professionally.

This is about presenting yourself in the best light, no pun intended. Set up shop near a window if possible. Natural light is the best. You want the light to be between your two and three o'clock. If you need more light, opt for lamps before overhead lighting. For seating, you want the camera at eye level, so it's not angled up or down. If you can't find the proper table height, get creative. Sit on the floor and try your coffee table. Then, consider your frame and be mindful of your background. Look for shelves and move some plants around.

It’s okay to have
different versions
of yourself

Some people don't like this rule. It's much easier to “be yourself” and to hell with the rest. But that's not how humans work. The way I behave at a networking event is not the same way I behave at a happy hour with friends. When emailing my family, I sign off with, “Love you bitches,” (it's a term of endearment in our house) but I end my Linkedin messages differently. Yet I'd argue I'm “being myself” in all these scenarios. Just the appropriate versions of myself for the situation. Think of it this way. There's the Golden Rule. This is the Platinum Rule. Treat others the way you know they'd like to be treated.

Clean up your digital profile illustration

You change in life
(so you should online too)

Clean up your digital profile illustration

Someone has probably waved a finger at you while saying, “Once it's on the internet, it's there forever.” It's time to wave one back at them. Take control of your accounts. Go through old posts or photos and delete things that don't reflect who you are anymore. I recently did this on my Twitter account. Not that there was anything cancel-worthy, but I'm not as into sophomoric humor as I was in my youth. Is that a crime? It actually turned into a pleasant Sunday morning of flashbacks. And I feel like it's more representative of who I am today.

Make sharing personal

Instead of blasting everything to everyone on social accounts, make it personal. If it's a photo of your food, think about a friend who loves cooking. Send it directly to them with the recipe. Same goes for songs, hiking trails, articles and random animal photos. You'll be surprised how quickly this will lead to engaging, personal conversations with a wide variety of friends and coworkers. And your followers will thank you (or rather me).

Say “thank you”

Digital communication is quick and saying thank you has largely been forgotten. Which means it's now an opportunity to stand out. Take 20 minutes, one day a week, and send thank you emails and/or texts to people who have helped you during the week. Everyone wins. You'll feel more gratitude for doing it. They'll start remembering you as a positive, appreciative person.

Intimate digital conversations illustration

Be direct when
you’re being intimate

Intimate digital conversations illustration

I can feel your eyebrows raising. Hear me out. Intimacy is intimidating. And digital intimacy even more so, because you're adding technical components to an already complex emotional situation. So instead of assuming anything, be direct with your partner. Just like in person, you want to read the room. And there's no harm in asking what they like, what they don't. Is it a few texts? Is it a video chat? What's the goal of the evening? This may sound like the type of conversation that would remove wind from your sail, but trust me, the resulting confidence will do just the opposite. It frees you up to get creative and maybe a tad explicit. But please, as a general rule, don't include any emoji.

Pass It On

Being a virtual gentleman is a journey. Not a destination. So share what's working for you with friends and solicit tips from people you respect.

The Smart Way
to Start Your Day

The Daily Valet. is your cheat sheet to what's happening, what's cool and what's making headlines. It's your secret to being the most interesting man in the room.

More on
Being a Gentleman