The Modern Man’s Handbook To Winning The Dating Game

If you DON’T think dating is a competition, just talk to the men who always feel like they’re being ignored, passed over, or “friend zoned” while the woman they’re interested in chooses another guy.

This may be an unpopular stance, and likely a taboo way to describe it, but as someone who spent the first two decades of life “losing” (repeatedly) at the dating game, I can assure you that it feels more like a competition to men than we let on.

Each time a woman selects a different man than him, the man in question will start to wonder why. What didn’t he bring to the table? Why is that other guy “better” than him?

The truth, though, is that it’s not about being better or worse, it’s about compatibility.

Absorb this: Someone can be “better” FOR a person than you. That doesn’t mean they’re a better person THAN you.

They may, however, be better AT dating than you. They understand the principles of attraction, manners, etiquette, romance, and what could loosely be referred to as courtship.

The primary reason I started coaching over a decade ago was to help men and women alike understand both themselves, and others, better. To build a stronger sense of confidence, create a life that they were proud of, and then have the tools to go out into the world and attract the right partner for them.

In the points below, we’ll focus on the men in particular, and what the ones who “win” do differently than the ones who “lose.”

(Inevitably whenever I write an article about men, there are comments that say “what about women?” or vice versa. Let me reiterate — this particular article is about men. I have literally hundreds of others about women…but not this one).

1: They’re honest about what they want.

Any healthy relationship in any area of life is built on a foundation of honesty. If there’s even a small doubt about whether or not someone is telling the truth or being genuine in their actions, it’s going to permeate into all parts of the relationship and begin to sew further doubt.

Dating, today, feels more fragmented than it ever has in the past. You’re talking to a few people at a time, swiping on a couple of different dating apps, one person falls off for no reason, the other ghosts you, and another yet starts saying all sorts of weird things to earn a *block* online.

Simultaneously, you’re dealing with pressure from family, friends, and yourself.

How can you ever tell what any of these people even want?

The men who win, the men who cut through the noise, are the ones who do it with honesty, authenticity, and consistency.

They show you, over time, that they are serious about getting to know you through consistent communication. They don’t drop off for days at a time. They don’t make a date and then disappear until the day of that date, making you wonder whether or not it’s even still happening.

Gents, women are so used to (but tired of) guys who flip flop on their feelings, guys who run hot a cold, guys who are inconsistent — that the thought of a man who’s actually honest about what he wants feels like winning the lottery at times.

It’s far better to be up front from the start, than it is to lead someone (or yourself) too far down the wrong road.

There is no room among the gentlemanly for dishonesty.

2: They show interest through real effort.

Great, you’ve been talking for a bit on and it’s come time to invite her on a date!

Most guys resort right to “wanna grab a drink?” texts.

Or, worse, “wyd” texts for a last minute invite. (What are you doing?).

Women understand that your amount of effort indicates your amount of interest.

Nothing about a casual text or last minute invitation makes her feel special. It doesn’t feel like you’ve put any thought into it, or that it’s even really about her. It just feels like you got bored, or have some free time, or could’ve sent that text to 15 women and went out with the first one who replied.

If you want to actually stand out, put real effort into not just the date you plan, but the conversations you have with her (more on this in a minute). As you learn more about her, the better you can plan something that suits her interests.

“James, most people don’t customize a date based on the woman’s interests!”

Yeah — that’s exactly my point — don’t be “most people.”

3: They have real and meaningful conversations.

Oscar Wilde said “conversation about the weather is the last refuge of the unimaginative.”

In other words, talking about the weather is boring and lazy.

Most people resort to topics like this, though, because it’s easy. Everyone around you is experiencing the same weather and it’s a low hanging fruit as far as conversation goes.

From the first time I ever read this quote, though, I’ve never once began a conversation with this topic. I don’t want to be seen as “unimaginative,” or boring, or lazy. I want to be memorable.

Men who win the dating game are memorable.

They actually care about the person they’re talking to, and show that through being inquisitive and curious. They ask questions that really matter, that go beneath the surface, the answers to which will be unique to this particular person and nobody else.

If you’ve been reading my writing for awhile you know that my wife and I met during the very beginning of the pandemic lockdowns. We talked online, all day every day, for nearly three months before we actually met in person.

You do not maintain this level of conversation for this amount of time by resorting to boring or tired topics. One (or both) of us would’ve lost interest long before we even met, and we’d never be building the life together that we are now.

You’re not a master conversationalist? Worry not, good man — asking questions is a lot simpler than you think. Listen to the answer, then ask another one based on that answer. Answer what she asks you in return.

Be curious. Be genuinely interested in who she is and what she’s about. If you’re really interested in potentially starting a relationship with her, you need to learn just as much about her as she does about you.

4: They never rush anything.

We live in an instant gratification era. We’re used to having everything presented to us instantly at the click of a button. We can order whatever we want through our phones and have it show up at our house — we can even buy a car online now, too.

All the while, we’re scrolling through Instagram and being bombarded with reels and images of everyone who already seems to be living the life that we’re striving for, creating an even more rushed sense of urgency to get there ourselves.

Life in general seems to be a lot more rushed than in past generations.

Unfortunately, many bring that mindset into their relationships as well. The patience and understanding needed to move at a slower pace, to build a strong foundation step by step, is seemingly waning as the years pass.

We want it all, and we want it now.

This, though, is not how human beings work.

Despite how the world around us changes, our biology evolves at a far slower pace. We are still humans with needs, wants, comfort levels, boundaries, and standards.

Most men are out there trying to move through the steps of a relationship (ahem, you know what I mean…) as quickly as they can, but this feels hectic and chaotic to a woman who needs to move at her own pace.

It also feels like you’re not truly serious about building a future together, because a future is going to last forever — and forever has no need to be rushed.

If you are genuinely interested in someone, you’ll never force or pressure anything to happen before its natural course. If things happen to move fast, great! If they need some more time to evolve, great!

The man who is patient is going to make a woman feel far more comfortable than the man who’s in a hurry, which will create space for trust, respect, and love to grow.

5: They learn how to build attraction.

This one eluded me for a long, long time (hard to believe, I know!)

That was a joke…

Here’s the thing, though — a lot of guys really have no idea how to create a layer of attraction on top of the “friendship” that’s so important at the foundation of a relationship.

As such, they check the friendship box, but not the potential partner box, and become fervently frustrated as a result.

Attraction is as much about excitement as it is about safety. She needs to feel comfortable and safe in your presence, but also a sense of adventure that makes her heart start to race.

Here’s the other part most guys get wrong — it’s not about your appearance.

It’s no secret that men are far more visual than women when it comes to attraction, but so many men only see this through their own lens that they forget how differently women think.

This is great news! Because you don’t need the chiseled jawline or 6-pack abs to be an attractive man.

It’s about seeing her for who she is. Living a life that you’re proud of. Honing qualities like ambition. Living with purpose. Showing up in positive ways for those around you. Building an internal sense of confidence that is projected through your actions.

And, yes, escalation at a respectful and comfortable pace. You don’t just lunge in for the kiss — you start with a grazing of the hand, an arm around the shoulder, a short and playful hug — and you feel her response to each one. If there is any hesitation or pullback from her, you do not escalate to the next step.

Each one that is welcomed and reciprocated, though, is a sign that you can move to the next when the occasion arises. This shows respect of her boundaries, and also that she is desired.

When you can make her feel both respected and desired, attraction will inevitably grow (as long as she feels the same in return).

6: They understand the basics of dating etiquette.

Men who hold themselves to higher standards will operate with higher levels of conduct.

This article is about setting yourself apart, so you simply cannot do things the way that everyone else does.

If you ever think to yourself, “James, nobody does that these days,” remember that is exactly the point.

In the matters of dating:

• Call, don’t text the invitation — but ask permission to call first in order to respect her time.
• Offer to pick her up, but respect her decision to meet you there.
• Make reservations, don’t run the risk of awkward wait times.
• Always arrive first, never keep her waiting.
• If you’re going to dinner, she follows the host/hostess to the table, and then you follow her.
• Always walk on the street-side of the sidewalk.
• If she doesn’t like what she ordered, offer to trade plates with her.
• Open doors for her.
• Pay all of the bill.
• Offer to walk or drive her home, and again, respect her decision if it’s a “no.”
• If a kiss feels welcomed, then go for it, you fool. Waiting too long can signal a lack of attraction on your part, which could blow the whole thing to bits before it even begins.

Small but noticeable things as you begin dating are exactly what will set you apart from the pack, because most men aren’t even aware these pieces of etiquette exist (there are many more), let alone do they follow them.

7: They present themselves well.

“James, are you saying a guy has to dress a certain way to be attractive?”

The only way a man (or woman) should dress is in the way that they want. The style that they feel expresses their personality, makes them comfortable and confident, and shows the world who they are.

There is no “right” or “wrong” style.

There is, though, appropriate for the occasion.

There is proper fit and finish.

There is attention to detail.

There is body language.

There are, most definitely, first impressions.

These things are all a choice. A conscious decision you can make in order to ensure that you’re being perceived in the way that suits you best by the people around you. In this case, a potential love interest.

Plus, showing up properly put together is a signal of respect and interest. It says “I actually care about how I present myself to you so I put in the effort.”

8: They put their phone away.

If you’re with her, be with her.

Our attention is so divided these days that it feels impossible to just stop and focus on one thing — or one person.

That, though, is the essence of human connection, which we’re seeming to forget.

“But James, my phone is upside down on the table.”

Yeah, which still looks like you could flip it over at any time and look at it, which you probably do.

It still sends the signal that something might pop up on your phone that is more important than the person in front of you.

Listen, if you’re an on-call doctor, or waiting on a call about a merger, or are the President of a country, then I (and she) will understand the need to monitor your phone. But, if this is the case, be sure to communicate it to her so she doesn’t get the wrong impression.

The point here is that in a world where people are trying to juggle 500 things at once, giving her your undivided attention is one of the greatest gifts, and one that she will notice and appreciate.

9: They don’t “sell themselves.”

Here’s a trap a lot of guys fall into — they think that they need to impress the woman they’re on a date with, and they go about it in entirely the wrong way.

They start name-dropping famous friends, bragging about the revenue, and the house, and the cars, and the success — and then they wonder why women only want them for their money.

Women read this as you needing to prove something to not only her…but to yourself.

You’re not secure and confident enough in your own accomplishments to let them speak for themselves over time.

If you’re that great, that successful, have that much going on in your life…it’s probably going to be obvious. And, if it’s not, it will become that way over time.

She wants to know who you are underneath all of that. Who is the man that worked his ass off to achieve this success? What values does he hold? How does he treat those around him?

Remember that you don’t attract what you desire, you attract what you project.

If you lead with the material stuff, you’ll attract those who are only seeking it out.

If you lead with kindness, compassion, calmness, and integrity, that will send a much stronger message that you won’t need to say out loud, because it’ll be projected through your actions.

10: They accept rejection with class.

“James, if you’re getting rejected, you’re not winning the dating game!”

We all get rejected. We have all gone through heartbreak. Nobody is undefeated in the game of dating, or the game of life.

Like any other area of life, though, oftentimes how you handle the difficulties will shape how you approach the victories.

Not to mention, communities can be small — and even smaller now with social media. If you fly off the handle, or become harsh or insulting when rejected, there’s a high chance that other people are going to hear about that. Your conversation might even get screenshotted and posted online.

At the very least, her friends or family may hear about your outburst, and your name will forever be blacklisted by anyone that she knows.

Not to mention — perhaps the timing was off. What if, down the road, she enters a new phase of life that you fit into better than you do now? You’ll have completely demolished that chance with your emotion-driven actions.

If you handle rejection with grace and class, you’ll show yourself as well as her that you operate with dignity even under duress.

The only thing that happens when you freak out over rejection, is that you show her she made the right choice by rejecting you.

11: They treat EVERYONE with equal respect.

Obviously she’s going to pay close attention to how you treat her, but she also understands that a lot of guys put on an act in order to get what they want.

The real reflection of your character is how you treat people that you’re not trying to impress.

How do you treat the bartender? The valet? The barista? The doorman?

How do you respond (not react) if your order is incorrect? Or if someone bumps into you?

She’s going to notice all of this, because she’s looking for consistency in your actions. Those actions are driven by your identity, meaning, who you really are at your core.

If you show up from a place of kindness, it’ll shine through in all of your interactions, not just the ones you have with her.

She’s looking for compassion, for caring, for signs that you value humans equally, as this means you’ll value her and those she loves, as well.

I’ve said it before and I’ll say it again: A nice person who’s rude to the waiter is not actually a nice person.

12: They’re driven and ambitious.

“James, finally you admit it! Only men with money win the dating game!”

I believe this to be a tragic misunderstanding among most men.

There is a big difference between women who just want money, and women who want men whose qualities empower them to make money.

Let me clarify this:

Men who are driven, ambitious, confident, and passionate about their mission, have a higher chance of becoming more successful.

For a woman who’s looking for a life partner (NOT a “gold-digger”), those are inspiring and attractive qualities.

It just so happens that those qualities also serve him well in his professional life.

It can also be true that he doesn’t have a lot of money.

Perhaps his ambitions are for a charitable cause or volunteering.

Perhaps he is in the building stages of a new venture.

That doesn’t change that he has the inherent qualities that she is looking for.

She is driven towards her own path, making her own accomplishments, creating her own legacy in her own life.

She’s not looking for your wallet — she’s looking for a teammate.

13: They’re dedicated to self-improvement.

Life is about growth.

Growth, in a relationship, must be a shared value.

You cannot have one partner who’s committed to growing, learning, evolving, exploring — and one who is content in remaining the same place their entire lives.

The two will simply not understand each other.

Men who “win” at the dating game are the men who are taking care of themselves.

They value their physical, mental, emotional, and spiritual health.

They’re inquisitive and curious about the world which keeps them interesting and gives them more to talk about.

Their interests are varied which presents greater opportunity for adventure and learning together.

They’re open minded which creates an opening for her interests to enter his life as well.

They are more aware of their own areas of improvement and therefore don’t shut down or become defensive when they’re recognized. They’re self-aware, and always working to become better each day.

14: They’re confident.

Come on, man. You don’t need me to tell you that women are drawn to confident men.

But…why?

Confidence (NOT arrogance) signals a certainty within one’s self. Confidence is not an accident and must be built over time.

It shows that you’ve built trust with yourself, credibility with yourself, that you’ve done the inner work in order to become stronger, more stable, more secure in your life.

It shows that you’ve got the ability and willingness to improve.

It shows that you’re willing to face challenges — of which there will be many in a life together.

Confidence faces problems alongside of her.

Confidence is calm and patient.

Confidence is secure in itself.

Confidence is not easily threatened or manipulated.

Confidence is certain.

15: They’re secure in their own identity.

Who are you, really?

Who is the man that she’s considering building a relationship — or even a life with?

I don’t mean what you do for a living, I don’t mean what your family looks like, I don’t mean any of the “external” factors we often define ourselves by.

I mean who are you?

What are your values, beliefs, worldviews? How do you represent yourself to yourself in your own mind? Who is it that you’ve worked to become, and continue to evolve into over time?

Life is a journey of discovery — both of the world and of ourselves within it.

Understanding what drives us gives us the ability to navigate this journey and make the right decisions that are fully aligned with who we are.

It empowers us to choose the right partner, the right path, the right career — and to be energized by those choices.

It makes us stable and secure.

It shows her, too, that you’ve done the inner work and are this man today, as you will be for the rest of your life.

That’s the level of commitment and consistency any woman (or man) needs to be sure of before they dedicate their entire life to you…

The truth is that you don’t have to be the perfect man to make her happy, she knows that doesn’t exist…

You just need to be the man you said you were when you first met her.

If that’s who she loves today, that’s who she wants to love forever.

Make sure it’s the real you.

• Click here to book a free call to see if we’re a fit to work together. My private clients find themselves living more confident, purposeful lives and cultivating healthier relationships with those around them.
• James Michael Sama is an internationally recognized speaker, author, and personal development coach.
• Finding success in creating hundreds of viral articles and videos on building limitless confidence and healthier relationships, James has accumulated over 39 million visitors to his website and a collective social media following of over 400,000.
• James speaks at live events and in the media across the U.S. and has become a go-to expert with outlets such as CNN, Bravo, The New York Post, The Huffington Post, The Daily Beast, CNBC, The Boston Globe, CBS, and more.