Confident Man in Room

Who’s The Most
Confident Man In The Room?

Imagine you just walked into a bar. 

You walk to get a drink and introduce yourself to the bartender. After talking for a bit, he offers you the chance to win free drinks. He says he wants to play a game.

He gets to point out three guys. Through only observation and a short description, you have to figure out who is the most confident man in the room. If you get it right, drinks on the house.

The bartender warns you that the answer isn’t obvious. And in fact, every other person who’s played tonight has gotten it wrong.

The Best Of The 3

Man A is wearing a custom-tailored Italian suit and a Rolex. He looks dapper. He’s surrounded by his entourage and other partygoers gawk at him. Everything about him says high-status.

The bartender explains, “That guy is an executive of a holding company. He’s worth millions, on the board of multiple non-profit organizations, and hosts some of the most prestigious events.”

Man B is chatting up two beautiful women. He’s loud, gregarious, and animated — the women love it. He’s physical and playfully dances with them. They’re giggling and can’t stop smiling.

“That guy is social with every attractive woman. He’s a real extrovert. He’s always witty and seems to know exactly what to say. I’ve seen him take home more girls than anyone else.”

Man C is leaning against the wall, off to the side. He’s in a t-shirt and jeans. He sips his drink and casually glances around the room. He isn’t talking to anyone and no one is talking to him.

“That guy is a software engineer. He’s quiet and generally keeps to himself. I’ve only occasionally seen him talk to people.”

The bartender looks at you and asks, “So who’s the most confident man in the room? Is it Mr. Status, Mr. Social, or The Loner?”

If you chose Man A or Man B, you’re wrong. Even if you chose Man C, you’re wrong.

The only right answer is…

Any one of them.

Evaluating Each Man

Man A

Just because Man A is successful, doesn’t automatically mean he’s confident.

What if he bases his entire self-worth on his wealth and status? What if he spent his life trying to prove that he’s good enough through his accomplishments? All of that could be taken away in an instant if his company went under.

Maybe he dresses flashy to constantly demonstrate his value because he feels insecure without that validation. Maybe he feels people and women will only like him based on what he can offer.

Confidence that’s built on material possessions isn’t very confident at all.

Man B

How about Man B? He has to be confident, right? He’s amazing with the ladies and a real charmer. That’s great…if that’s who he actually is.

But what if it’s all a performance? What if he puts on a mask pretending to be this over-the-top, suave extrovert? When in reality he’s an insecure wreck who memorizes lines and routines to feign genuine conversation. 

Maybe he does all this because he feels like a loser if he doesn’t “win” every woman over. He chases that validation night after night but is miserable since no one knows the real him. He bases his worth on empty sex that never really fulfills him.

Sound far-fetched? I used to be that guy. I was getting laid but couldn’t be any more lonely.

Man C

But surely there’s no way Man C could ever be the most confident. He’s a loner and doesn’t choose to interact with others. He’s probably terrified of talking to new people or getting rejected.

Those are a lot of assumptions. What if he’s not actually anti-social?

Maybe he got out of a long relationship and isn’t ready to date right now. Maybe he comes to the bar to enjoy his favorite cocktail. Maybe he has a girlfriend and simply likes to unwind after a long day of work, listen to the music, and people watch.

He doesn’t need to talk to people in that moment because he’s content. He’s open to conversation but is happy hanging out and relaxing. He’s having a great time without having to impress other people.

That seems self-confident to me.

Confidence Isn’t Skin Deep

The point is that any of these guys could be confident or not.

The determining factors are not about what they look like, where they work, who they know, or even necessarily the behavior they demonstrate. 

It’s about how they perceive their worth and if their actions align with their intentions.

Therefore, the more important questions are…

  • Who’s showing their true selves? vs Who’s acting?
  • Who loves himself for himself? vs Who bases his value on external sources like money, women, or outside judgment?
  • Who’s doing what they want? vs Who’s doing what they think other people want?

Only the vulnerable man who is unashamedly himself possesses true courage.