What are Men thinking on the First Date?

Key Takeaways

  • I break down your potentials as 3 types of men you might encounter on a first date: The Newb (nervous but genuine), The Playboy (confident but short-term focused), and The Gentleman (looking for a long-term connection).
  • Each type has different priorities and tells on themselves through their thoughts and behavior. Watch out for red flags (e.g., The Newb mentioning his ex, The Playboy oversharing, The Gentleman ghosting you).
  • The right date for you depends on what you’re looking for. The Newb is good for patient and empathetic women, The Playboy for confident women okay with something casual, and The Gentleman for women ready to settle down.
  • I offer tips on how to identify each type and their intentions through their conversation and actions.

What are Men thinking on the First Date?

Have you ever wondered what goes on in a man’s mind that is sitting across from you? 

Is it a whirlwind of witty banter or a silent panic attack disguised by a charming smile?  

Do you want to know if we analyze your outfit or rehearse pick-up lines in our head? 

I will give you a peek into the different thought patterns of three common types of men on a first date.

I will tell you their thoughts, priorities and the red flags to watch out for.

So, get ready to laugh and maybe cringe a little, by what men are REALLY thinking on a first date!

The Newb: 

Fresh to the dating scene or perhaps recovering from a failed long term relationship, this guy is likely a ball of nervous energy. 

His thoughts are a whirlwind of self-doubt.

He may overthink jokes, analyze every word, and secretly rehearse future dates in his head.

He’s genuinely interested in getting to know you, but might struggle to fully relax and be himself due to his anxieties.

Things he will tell himself:

“Okay, don’t mess this up.” 

“Smile, make eye contact, be interesting… but not too interesting.” 

“Did I put too much cologne on? “

“Should I have worn a different shirt?”

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First Date Priorities

His priorities you may actually find cute. 

What he’s worried about most is making a good first impression and how to keep the conversation flowing. 

This guy will try to avoid awkward silences at all costs! He just wants to get to a 2nd date if possible, so he can be himself.

You may read into these anxieties the wrong way and think that you’re the problem or that he’s just a weirdo.

But I promise, it’s his own negative self talk that is getting in his way.

First Date Red Flags

The big red flag with this guy is mentioning his exes. You can chalk this one up more to his anxiety than his level of interest in you.

But either way, it’s not a good look on a first date.  

You want a guy that is ready to make you a priority, not someone that is still thinking about another woman.

This is not fair to you and shows a lack of emotional intelligence on his part.

Which is why he’s a newb. He’s still learning to take your feeling into account.

If he mentions his ex, even once…he may still have some things to work through on his end. Proceed at your own risk.

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First Date Green Flags

Showing Genuine interest in you.

If he’s giving you lots of eye contact and is enjoying listening to you talk, that’s a good start.

If the conversation is an easy back and forth that’s a good sign that you guys are compatible. 

All healthy relationships have a foundation of compatibility and friendship. So if you are getting that on the first date, that’s excellent.

Especially with a nervous newbie!

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The Playboy

This man has been on his fair share of first dates. 

He’s comfortable navigating the initial conversation and will be very confident in his approach

However, his thoughts might reflect a more analytical perspective. His questions will be more self centered.

It’s not because he’s cocky, but his confidence is basically telling him that he’s the only one that can mess things up.

He’s still looking for a genuine connection, but his past experiences will influence his evaluation of you as a date.


“Let’s see if there’s a spark here.”

“I wonder will she find this funny?”

“I wonder how she will react if I say ______?”

“Does she seem like someone that will kiss me at the end of this date?”

“Is this date living up to my expectations?”

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First Date Priorities

The Playboy is the guy that gives others a bad name. 

He has a more short term view on relationships

And that’s ok, except that he rarely tells you that up front. 

It’s not that he’s only looking for sex though. That’s a common misconception. 

This guy places a high priority on finding common interests as well. 

As a matter of fact, 

those common interests that you share is what makes the relationship last longer than 

they’re supposed to. 

Compatibility is huge with this type of guy and every move he makes is with assessing 

the potential for the next date in mind.

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First Date Red Flags 


His confidence will lead him to overshare alot. 

You have to pay attention to this because this guy will often tell on himself. 

For example, if he starts talking about the last girl he went on a date with, 

pay attention to the story. 

Listen for anything that you wouldn’t agree with that he did or said. 

Those will be some things that he may say or do with you as well. 

First Date Green Flags 

Positive attitude.

One of the things that undoubtedly drew you to him in the first place was his positive attitude. 

Playboys tend to have a great sense of humor. 

That energy is given off and received by you as confidence. 

There’s nothing wrong with that. 

There’s nothing wrong with dating a Playboy long term as long as you understand his game. 

You should not try to change him, but wait for him to mature and realize your worth. 

Then you can have your cake and eat it too.

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The Gentleman

This man is looking for a meaningful connection, not just a casual fling. 

I’m not saying he won’t accept one, just that it’s not his primary objective.

His questions to you will be deeper than surface-level topics. 

He will be curious about your aspirations, dreams, and relationship goals. 

He’s genuinely interested in getting to know the real you, 

and his internal dialogue might focus on potential: 

“Can I see myself with this person? 

Do our life goals align?” 

He’s likely more cautious and selective, but if he feels a genuine connection, 

he’s more likely to invest time and effort into getting to know you better.

He is just as confident as the Playboy. 

But his thoughts are all about compatibility.


His thoughts will be more introspective than the other two types of guys:

“Do we have similar values and interests?”

“Can I imagine building a future with this person?”

“Does she have the same level of emotional intelligence and communication skills as me?”

He’s paying close attention to shared values and future compatibility, 

while still enjoying getting to know you.

He might still try some of the same moves as the Playboy

But the difference is that The Gentleman has a long term goal in mind.


First Date Priorities

The Gentleman’s priorities lie in enjoying your company. 

He’s trying to build a connection.

He’s exploring potential for a future together.

Every move he makes will be with those goals in mind.

He is closer to settling down than the Playboy. 

I compare these two because women often get them confused.

The crucial difference being 

The Gentleman is more mature and ready to settle down. 

First Date Red Flags

Ahh but we all come with red flags and the Gentleman is no different.

He’s the heartbreaker. 

You will have an amazing date, a great restaurant, a door opened for you, amazing conversation.

And then nothing.

You will be ghosted if he’s not interested. 

To save yourself from this embarrassment pay attention to how he’s acting on the first date.

Did he feel disrespected at any point? 

Were there any disingenuous moments that happened during your conversations?

Are your core values compatible?

Unlike the others, the Gentleman isn’t going to argue or debate you at the dinner table 

He will let you have your say, agree to disagree, and then just move on.

So if the connection isn’t 100% authentic, 

You will either have to adapt or prepare to move on.


First Date Green Flags

Genuine interest in your life.

The Gentleman has no poker face.

He’s looking for a long term partner. 

So if you guys are talking and he’s interested…keep talking.

You will know if he has genuine interest if he starts to insert himself into your scenarios.

For example, you mention that you live 45 mins away from work.

If his response is “oh wow, I stay about 45 mins away also, we could car pool!”

That’s not just game he’s spitting. 

He’s trying to figure out a way to spend more time with you. 

That is a good sign if you are interested in him as well. 

Best Man for you to go on a First Date with

So which is best for you specifically?

You absolutely can tell from a first date.

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Who is The Newb a perfect first date for?

Newbs are great dates for women who are patient and understanding. 

The reason being is because you won’t take their perceived weirdness as a negative. 

Newbs are also great first dates for you if you’re a woman who is very empathetic. 

Those guys will be nervous at first, 

so you will be more apt to understand how they are feeling at the moment. 

Finally women who are newbs themselves! 

If you are just now getting back into the dating scene, 

the last person you want to date is a Playboy! He will smell fresh meat! 

Find another newb, someone who’s on your same comfort level. 

And see if there’s a spark with someone that won’t be as aggressive as the other types of guys.

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Who is The Playboy a perfect first date for?

So you’re wondering, who the hell wants to go on a first date with a playboy! 

Ok, maybe you’re not because that would be a rhetorical question. 

Alot of women love the bad boys. But only the most confident can handle them. 

If you’re a woman that is not looking to settle down yet yourself, 

then he’s the guy for you. 

Plenty of very good, long lasting relationships came out of this phase. 

These are the couples that grow together. At the same pace.

The ones you saw in their twenties and thought were a train wreck waiting to happen…

but here they are 20 years later and still together. It’s all about compatibility. 

Who is The Gentleman a perfect first date for?

If, though, you are ready to settle down. You should be looking for a Gentleman as a first date. 

They have already passed through the Newb phase. 

Through all of those dates their confidence has grown. 

They breezed through the Playboy stage and had their share of one night stands and live in girlfriends. 

Believe it or not, those experiences teach us what we want and don’t want in a partner. 

So by the time some of us graduate into the 

Gentleman phase we have a clear image of what we want our wife to look like. 

And if you pay attention on your first dates, you will hear all of the clues.

what men are thinking on the first date

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