Classic Dating Etiquette For The Modern Gentleman

Chivalry isn’t dead, it’s just evolving.

James Michael Sama
9 min readFeb 13, 2024


Building a relationship with someone is a tricky thing. It takes proactive and deliberate action — yet it’s not something that comes with a formula or blueprint. There are no guarantees, yet there are strategies you can put in place that work in your favor.

For men, we are traditionally the pursuers in dating. While this [so far] remains true, society is progressing all around us. Women are out-earning men and out-performing them educationally.

My high-performing female clients find this to be a challenge, because men shy away from them, which I believe is a result of men being confused about their role in society or in the relationship.

They’re not quite sure what value they can bring to the table, as they’ve been conditioned since, well, forever that their primary contribution to a marriage or a family is financial. Men have been the supporters, providers, and “breadwinners” for countless generations.

The value today, gentlemen, is not monetary. We must shift our perspective and step up to the plate in new and innovative ways to add value and stand out from the crowd.

Here are fifteen often overlooked details to pay attention to in your dating life that make all the difference in expressing that you’ve got more to offer than just what’s in your bank account.

1: Be honest about your intentions.

First thing’s firstthere is nothing chivalrous or honorable about leading a woman on, or being insincere simply to get what you want.

I hear it all the time — women are confused about what the man they’re dating is even feeling. He’ll say one thing, and do another. He’ll be cute and romantic, and then disappear for days. He’ll be confused or unsure about what he even wants.

No, women shouldn’t stick around for this type of behavior, but that’s a point for a different article.

It may not seem like a big deal to you if you’re just not feeling it and decide to stop answering calls or texts one day, but actions like that can really linger in someone’s mind and cause trust or self-worth issues.



James Michael Sama

I help you evolve into the ultimate version of yourself. Life & Executive Coach. Multi #1 writer. Trusted by: CNN, CNBC, NY Post, CBS, more. Say hi! @JamesMSama