The 4 mistakes that’ll kill your first date

Ah, first dates.

First dates, first dates, first dates.

Don’t you just LOVE the uncertainties and anxieties of meeting up with a lady you barely know for the first time?

“Golly gosh, I can’t wait to show this cool girl my Yu-Gi-Oh card collection when I take her to my place. She’s gonna be so astounded when she sees I have THREE Blue-Eyes White Dragons”

Will you two hit it off and want more of each other?

Or will this one end up as a funny and/or depressing story/learning experience?

(In any case, you’ve both unconsciously pre-consented to whatever you’ll be getting out of the experience. But that’s too deep and esoteric a topic to get into here)

The grey area between those two scenarios is where this post’s wisdom comes in. When you’re not entirely set on each other, but the vibe’s there and you’re both interested in seeing where it goes…

Here’s how to stop your first date with that pretty lady from sucking, and to ensure she wants to see more of you. Avoid these 4 common first date mistakes while also being a gentleman, a savage, and a ray of sunshine, and you’ll have a good time with her!

Mistake #1 -Interviewing her instead of vibing with her

“Where are you from?”

“What do you study and/or do for work?”

“What do you do for fun?”

Necessary things to know about someone, for sure. But the obvious problem here is – These questions are BORING. You can have these conversations with absolutely anyone. You’re not on the date because you want a conversational partner. This girl is someone you could end up having intimate fun or even a lifelong commitment with. Act like it.

“So, can you tell me more about your time with your ex? What responsibilities did your role entail?”

Small talk is a necessary step towards more intimate, deeper talk, but it DOESN’T have to be boring and formal and formulaic.

I like to make small talk fun. When I first meet a new girl and the inevitable “what do you do?” small talk comes up, I like to turn it into a guessing game. I enjoy watching the girl smile and light up as we attractive, mysterious, sexy strangers try to figure each other out with our intuitions and observational skills.

Get used to making ASSUMPTIONS about a girl. This is a fun, casual way to make small talk that’ll make you stand out from everyone else she can have a conversation with.

Instead of “where are you from?” (BORING), you can say “Are you from the west coast? Because you have that chill west coast vibe.”

“You look like you study engineering.”

“You look like you just got off work as a bartender.”

“You have such wholesome crackhead energy and I love it” (this is my favourite pickup line when I meet drunk girls on nights out who look like they’re having a wild, fun time)

“You’re dressed like one of those Instagram girls who’s obsessed with fitness. Please don’t tell me you spend all your free time at the gym and planning out your meals.”

And you can turn this back onto yourself. Ex. When a girl asks you “what do you do?”, rather than saying, “oh, I’m an accountant”, you can say “guess!” and let her have some fun trying to figure you out. Then if she gets it wrong, you can build on that before keeping the guessing game going.

“What about me makes you think I’m a doctor?”

Now, a lot of people who are chronically trapped in their heads have a tough time sharing themselves with others, including attractive dates of theirs, so rather than making the date about getting to know each other…

They make the date about getting to know a bunch of facts about each other. This makes the date DRAB and DULL.

If dating isn’t fun, you’re doing it wrong.

Real fun and intimacy and sexual excitement DON’T come from telling someone logical information about yourself. “I have an older brother who’s a lawyer and he lives in Colorado,” “I used to live in Arizona and I’d always hike up the mountains there”, “I learned Spanish from my mom’s Colombian side of the family,” “I was captain of my volleyball team in high school.”

Interesting, right?

Not really.

This is the conversational equivalent of reading a modern formal textbook about your date. You’re learning a bunch of facts about them, but they’re not really showing themselves to you. You want more of an “I’m watching a critically acclaimed classic movie about my date” type of vibe.

Turn these facts about yourself into stories.

“People can never tell I’m half-Colombian until they meet my mom. Her thick accent always gives it away.”

“I used to see scorpions when I’d hike up the mountains back in Arizona. I was always tempted to take one home and keep it as a pet. Do you think it’s attractive when a guy has a pet scorpion?”

You don’t have to paint yourself as some super-adventurous James Bond character. Just learn to find the fun and spontaneity in your mundane, unique life, and let the girl share herself in the same way.

If you can’t let go and simply VIBE with this girl… If your conversations are 100% serious and factual and formal and formulaic with little room for fun and spontaneity… Dump her. You’re dating the wrong girl, brother.

Mistake #2 – Imagining your future with her… When you barely know her

Is she your future girlfriend or wife? Will you end up introducing her as your beautiful other half to everyone you know? Is she the ONE for you?

Relax, my man.

You don’t know who this girl REALLY is yet. That’s why you’re going on this date with her – to assess your basic compatibility and to determine whether she’s a good fit for you and your goals in life.

You’ll figure out how good a fit she really is for you as time goes by. Don’t let your fantasies of her seduce you into delusion.

Pace yourself and your feelings for her, even if she checks all your boxes and you’re super super enthusiastic about getting to know each other.

Otherwise, your neediness will sink you. Your fantasies about finally finding the perfect girl for you will seep into your behavior, and sooner or later, you’ll do something that telegraphs an unhealthy level of investment in an imperfect girl who only MIGHT BE a great fit for you.

Quality women HATE IT when a man tries to jump into a strong relationship with them on the first few dates, even if that’s their goal too. She wants you to choose her because you like HER most out of all the girls you could have had (after getting to know who she REALLY is). Not because you’re enamored with your fantasy of her being the absolute best girl in the world.

To avoid this oneitis trap, keep your options open in the early stages of dating, even if a certain girl checks all your boxes. Hold her lightly, look at her objectively, and always be willing to walk away if/when she violates your morals, standards, or boundaries. You may like this girl, you may appreciate plenty about her, but your individual, personal connection hasn’t been built yet. So far, it only exists in your fantasies.

When you’re constructing a building, you lay the foundation first. You don’t jump right into building the highest storeys.

Be realistic. She’s not some amazing demigoddess of a girl destined to be your twin flame. She’s a person just like you, who also happens to be female and fuckable. She’s imperfect and flawed like every other human in existence. Treat her as she is, not as your baggage and fantasies would like her to be.

Mistake # 3 – Keeping the date going way too long

Look, I know you want a girl in your life you really connect with and enjoy spending time with.

But like we went over in the last point, pace yourself. Don’t expect to jump into a super strong relationship on the first few dates unless you’re both really desperate and have no hope of ever finding another good option.

A first date, assuming the vibe’s there and you’re both invested, should last 1.5-2 hours. 3 hours is the absolute longest a first date should go, and even then, you’re pushing it and you should save a date of this length for when you’re both CERTAIN the date is only getting better and better.

(also if she’s only in it for a hookup, in which case you know exactly what you’ll be spending hours 2 and 3 doing)

Any longer than 2 hours, and you’ll subcommunicate that you don’t have much to do with yourself. Your commitment to spending that much time with a girl you’re only starting to get to know comes off as needy, not romantic. Any shorter than 1.5 hour, and you’ll put way too much pressure on both of you to make something good of the date before your time runs out. The date will be cut short before it gets reeeeally good.

You want yourself and the girl to be able to relax and enjoy yourselves, but also understand that your date has a time limit and you’ll need to get back to your individual lives soon. 1.5-2 hours is the perfect amount of time for this.

I structure my first dates in two parts:

  1. We grab coffee at a classy place, do the initial “get to know you” chat over said coffee. This lasts about half an hour. If the vibe isn’t there, it’s easy for either of us to cut the date and leave.
  2. I take her on a mini-adventure after we finish our coffees, if the vibe between us is there. As we walk, I casually, naturally touch her while engaging in fun conversation. This lasts about an hour before I see her off.

Again, a deep relationship with a girl is built over time, not immediately discovered. Some girls are more compatible with you than others, and you’ll naturally click super easily with the greatest ones for you.

Even when you’re dating a great girl like that, remember that “the one” is chiseled, not discovered. She may be a high-quality blueprint, but the blueprint is only potential. It’s not a guarantee of a high-quality relationship.

Don’t throw away your self-respect for a fantasy girl.

Mistake #4 – Being dishonest to win her over

Dating a girl you can’t be yourself around is never worth it.

If you find yourself constantly consciously calculating what to say to her, what to do with her that’ll make her think you’re that cool guy she wants to be with, and you’re scared of saying or doing some Wrong Thing™ that’ll make her leave you…


It’s infinitely better to piss a girl off and make her hate you through being honest about yourself and what you value, than to hide your true thoughts and feelings away to keep her comfortable.

Settling for a girl is incredibly disrespectful to both her and yourself.

Even if she buys your dishonesty and keeps you around, you’re now dating a girl who’s sucking the life out of you and making you unconsciously resent yourself more and more. I don’t care what she looks like or how “great” your conversations are, or how many other options you don’t have. This girl will NEVER make you happy.

Don’t hide yourself away. Express yourself freely and genuinely. Show her your rough edges.

Be honest but don’t be boring. Show her the truth about you, but don’t give your entire self away early, and make getting to know you FUN, not a formulaic, formal encounter.

The more upfront, straightforward, and authentic you are about what kind of man you truly are… The more you craft your image from what’s TRUE about yourself rather than putting up a persona of being some perfect fantasy guy for her…

The more you’ll repel girls from you who’d never make you happy…

And the more strongly you’ll attract girls who have major common ground with you and WILL make you happier.

This is polarization. Polarization is a key concept in selecting women who’ll enrich your life.

You can’t win a girl over if you don’t risk being rejected by her. Play it too safe and generic, and you may get an abundance of girls superficially into you, but you won’t have anything meaningful with them. The girls you attract will be dime-a-dozen, and they’ll like you for your image, not for YOU.

You can’t be a powerful, genuine, intoxicating man to some girls without being a weird, repulsive, joke of a man to other girls. That’s just the nature of polarization.

If you want to strongly attract the girls who’ll make you happiest, you need to strongly repel the ones who’ll make you unhappiest.

You can’t get the Ws in your dating life without also taking the Ls. So embrace yourself, brother. Embrace 100% of yourself. Some people will dislike you no matter what you say or do, and that’s just life.

Focus on the people who are also ready to embrace all of you.

Anyhoo, I hope you got some value out of this article. I hate writing conclusions to stuff, so I’ll make this one brief.

When you’re ready to step into your most integrated, most aware, most masculine self, and to intimately understand how women REALLY work…

See me in one-on-one coaching!

Your first dates (and your second, third, etc ones) will only get better and better!

Take care,

– Ben

Leave a Reply