5 Steps to a More Successful First Date

There is one top trait all great courtesans possess – they know how to have a successful first date. I saw this play out time and again as their Madame and confidante, “everyone has good qualities, that is what I focus on during every date.” A courtesan is a professional dater, often with those she might not ordinarily spend time with. Her talent, the jewel that makes her rise to the top is her ability to let go and enjoy the date – a technique for first date success.


Enjoyment is the first date goal to aim for – not compatibility.


While it’s normal to aim for long-term compatibility, like minds share mutual interests, doing so before you even meet puts expectations on the date that doesn’t give it a chance to naturally unfold. It casts a shadow on our interaction and joy of the date.


man enjoying first date searching

There is a Buddhist perspective

 Clinging to the self is mainly an attempt to fulfill desires …
~ Dalai Lama, 1995, The Path to Enlightenment

When we want something we spend considerable time and energy thinking about it, 46.9 percent of our time is spent thinking about something other than the present.  We become fixated and attached to something being the way we want, rather than letting it organically flow. If the outcome is any way than what we envision, disappointment and frustration follows. Buddha says this is what leads to suffering – our desire and want causes the dissatisfaction.

If we equate a good first date to our level of compatibility, then our success and pleasure is contingent on those expectations.


One of the biggest factors to first date success is your own expectations & letting go of them. 


There is a difference between grasping for what we want the other person to be and simply experiencing those actions. By simply observing, instead of judging, we subconsciously let our fight or flight response go, our anxiety subsides, and we can just enjoy the first date.

We often hear the term just be present, here are some helpful ways to do that.


1)  View the first date as more like a meet and greet and not an interview

It’s hard not to analyze everything someone says or does or the way they look when you first meet them, it’s human nature, but try to let all that go and just enjoy the experience.

Go to your next first date without expectations

Expecting certain behavior traits or actions of them puts so much pressure on one thing – the first date – if feels like grasping.  If both sides don’t meet expectations, then it fails. This robs you of the opportunity to enjoy the date and the whole dating process.

When we plan a first date we have an idea what we’re looking for: kindness, physical attractiveness, an exciting personality, and income potential come out one top, according to science. We do this because we project ourselves with that person six months or even further into the future. We look at them through the lens of a long-term partner, and use the first date as an interview to determine compatibility.

Going to the first date with expectations, in defense of what we are expect of a long term parter detracts from who they really are. It’s not doing you a service, instead you’re robbing yourself and them the pleasure of the date and the simple pure joy of becoming acquainted.

This single act will bring you closer to enjoyment – the hidden true gem of dating


2)  Make the date shorter

Don’t plan an elaborate dinner, they may be nervous and not act as appreciative, excited or thankful for the effort you put in simply because they weren’t aware of the effort, and in the end this causes your own expectations to overwhelm you.

A simple technique to have a successful first date it look at the first date like an easy, carefree introduction


To me, this immediately sounds less stressful. It sounds less like a test and take pressure off expecting them to fit your mold, it takes the pressure off you fitting theirs, and it takes mounting pressure off the date itself. Instead of looking for ‘the one’ in them before you even know them, view the date as a way to get to know them. 

Going to a first date looking for ‘the one’ can feel like grasping, which isn’t fair to the date itself.

couple enjoying first date success

3) Go somewhere you enjoy

If you enjoy beer and pizza and you only do it on occasion, then do that. If you enjoy kayaking but rarely find the time, try that. If you saw a sake tasting class that sounds fun, go for it. Make the date something pleasurable for you and not so much about them. If they hate sake or don’t feel like kayaking, they will let you know.

Make a first date more successful by just enjoying it


For courtesans, a stress-free date is crucial, both sides must feel at ease for the date to flow. While a courtesan may not go to a date with looking for a life partner, there are still a number of factors that may affect her enjoyment (if she didn’t screen him, if the conversation doesn’t flow, if she’s ruminating over life problems, she can’t be present). If she lets anything affect her presence in the moment, it will affect her ability to be his ideal date and he won’t invite her on a second.

The more stress-free the date is, the date blossoms into an opportunity to enjoy –  the other person and the experience – which allows intuition and feelings of chemistry to develop, or not.

Don’t wait for sparklers and a bang. 


4)  Do something active 

Research shows if you do something that induces adrenaline on the first date you’re more likely to meet that person again, as adrenaline increases, so does the level of attraction.

For another science-backed way to use brain chemicals in your favor, read this article Date Ideas for Bonding – Laugh together and additional ideas for Spontaneous Date Ideas. 


5)  Give yourself a set number of dates

Two, three or even five before you consider them as a long-term option. Try to go into the date without analyzing who they are and whether you’re a good fit for the future.

Looking for ‘the one’ is ruining your first dates


There is a difference between intuition and expectation. Intuition is letting our gut, our instincts, tell us when something or someone might be good or bad. Expectations are a belief that something or someone should be or will be something, usually based on what we want. Expectations aren’t really a fair way to meet someone, they’re not fair to you or them or the entire dating process.

In reality, a first date is a 30-45 minute meeting between two strangers to see if you can have a conversation, feel for  chemistry, and provide an opportunity to pay attention to intuition. All of which is hard enough to do with a stranger when at ease.

The trick you can glean from courtesans is go to the first date without a list of expectations. Expectations put unnecessary pressure on the date and everyone involved.


You can reach first date success, have a successful first date, learn how to have a successful first date, discover how to make a first date more successful by following these five steps, watch the video below. 


A video version. 

YouTube Video Link





Related Posts

If you don’t like your story, it’s time to rewrite it.

Let’s Be Friends | Receive A FREE Fun EGift

A chapter of my book, The Las Vegas Madam

Scroll to Top