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Jan 15, 2025
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A Gentleman’s Rules for Dating

7 years ago
4 mins read

by Michael Satterfield

In today’s culture of swipe Left/Right
dating, Netflix and Chill, and “hanging out” it seems that the art of
actually dating a woman might be lost on the majority of men. If you are one of
those guys looking to impress a special lady here are a few things you might
try that will make you stand out among the flood of DMs she is getting every
day.

Personal Communication 

This is scary, but actually ask her out, in person if possible, or at the
very least on the phone. It won’t kill you, she might say no, but at least you
will have a clear yes or no. Trust me it’s better than the vague text reply
Emojies you are supposed to decipher. To make it easier try to have something
pre-planned you would like to take her to and put some thought into inviting
her to something you will both enjoy.

Something like “I would like to take you to an art gallery opening this
Saturday at seven if you are free, then afterward we can get dinner.”

It can be a movie, a play, event, church social, pretty much anything you can
think of, but by asking her to a specific event she has a clear idea of what to
expect and can make up her mind.

Transportation

If she agrees to the date, figure out transportation. Even if it might be
out of your way, ask her if she would like you to pick her up. Now, this could
mean pick her up from work, or home, or her master’s program at the university
clear across town, if she says yes, make it happen. If you are picking her up,
that means you are walking up to the door, texting “here” from the
parking lot is not acceptable. When you go to the door be prepared to politely
interact with family or friends she may live with. Now she may decline the
offer to have you pick her up and plan to meet you at the event for whatever
reason, just make sure that transportation is sorted out beforehand.

Bring Her Flowers 

Now, this might not be common practice anymore, but you don’t want to be
common, you want to stand out. It shows you are thoughtful and clarifies your
intentions are more serious. If all goes well she will take them home, put them
in a vase and they will be a reminder of you for days. They don’t have to be
expensive or fancy, just a token of your affection.

Dress Appropriately 

This doesn’t mean dress up in a suit if you are taking your date to a
baseball game, but put some effort into your style. If you don’t know what the
attire should be, a safe bet is “smart casual” some dark jeans, a
button-up shirt, a nice belt/shoes, and an appropriate coat. Be yourself, but
use the opportunity to let your style say something about you. She will
appreciate the effort.

If you are inviting a date to an event with a specific attire requirement, be
sure to let her know ahead of time.

Offer Her Your Coat

If it is cold outside, offer her your jacket. Similarly, if it is raining
she gets the majority of the umbrella coverage, etc. Her comfort should be
prioritized over yours.

Be Clear About Your Intentions

This is true regardless if you are looking for a casual dinner date or the
future mother of your children (you may want to hold off on proclaiming the
latter if you are on a first date). If you are interested in a woman and just
want to get to know her better, let her know that. If you have no interest in
her beyond just hooking up, you might want to just go back to swiping right.
But in all honesty, as much as we like to pretend women are the only ones who
are vague, men are just as bad. It’s not so much what we say, it is what we
don’t say, express your feelings, tell them what intrigues you about them.

Send A Thank You Note

This may sound odd since you asked her out, but after a first date, even if
everything didn’t go according to plan, send her a short note. If it went well
let her know that you had a wonderful time and you look forward to seeing her
again. It doesn’t need to be a love sonnet, just a brief note. If things didn’t
go well, send a note anyways, thanking her for coming out, and wishing her
well.

Open Doors For Her

The car door, the restaurant door, the theater door, the taxi cab door (if
she didn’t ride with you) any door you approach together you open for her, with
one exception, the door to her home.  After walking her back (If you are
dropping her off at home), you say your goodbyes and if she doesn’t invite you
in, you step back a step and let her get inside safely before leaving.  Remember, she is not obligated to
invite you in.

If You Invited Her Out, You Are Paying

Now I am assuming you are not a dupe who is asking out a woman who has no
interest in you beyond a free dinner and some drinks, but regardless, if you
invite her out, pay for the date. If she invites you out, offer to pay for
yourself and if she insists on paying, let her. This should evolve as your
relationship progresses.

Turning Off Your Phone

Nothing can spoil a night out more than the sound of your date’s phone
receiving messages and calls, or worse your date spending all night looking at
their phone. If you want to impress your date, give them your undivided
attention. Make sure they see you switch your phone off or to ‘do not disturb’
mode, today showing someone you are disconnecting from the rest of the world to
spend an hour wholly focused on them sends a message.

These are just a few tips guys should follow if they are hoping to stand out in
the world of dating. But what are your thoughts? Do you have a favorite tip
from the list or a tip of your own? If so please share in the comments below.

Michael Satterfield

Michael Satterfield is the founder of The Gentleman Racer, a leading automotive lifestyle site blending cars, travel, and culture. Known for its compelling storytelling and unique perspective, the site has become a go-to destination for car enthusiasts and style aficionados.

A Texan with a passion for classic cars and motorsports, Michael is also a hands-on restorer, currently working on a 1960s SCCA-spec Formula Super Vee and other project cars. As the head of the Satterfield Group, he consults on branding and marketing for top automotive and lifestyle brands, bringing his deep industry knowledge to every project.

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