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How To Date – Dating Advice vs. Dating Success

Cain Parish

In This Article:

When we think about how to date, we generally look for opinions. Crowdsourcing experiences and perspectives allow us to try and incorporate the logic of others into our own strategies – shortcutting the process of trying and failing ourselves. The problem with learning how to date, and many other similarly subjective fields, is that advice is given in general terms, where real life happens in specifics. Let’s understand what this issue means and how to solve it.

A woman looking up how to date on her computer receiving good advice

How To Date Just Like You’re Playing Sports

When you receive coaching in a sport, it’s a straightforward process. The coach works with you to identify your weaknesses. If you’re playing tennis, it could be any combination of elements that go into a great game of tennis – the serve, your forehand/backhand, your footwork, etc. When you’re working on your game, your objective is to develop the skills necessary to do the non-negotiable parts of the sport; hit the ball just so that it lands in the correct place for the correct reason.

It’s a straightforward process because there’s no getting around the objective – to win the game you are going to have to learn to hit the ball.

Dating, however doesn’t work that way. You cannot simply tell someone how to date other people by fixing their core fundamentals, because there aren’t any non-negotiables the same way there are in other skills. Sure, we can teach someone that’s never been on a date the extreme faux pas such as avoiding sneezing directly in your date’s face or showing up two hours late, but that’s the sporting equivalent of chasing your opponent around the court with the racquet.

The finer points of a subjective human experience are too nuanced to be able to give straightforward advice on how to date that actually has a tangible benefit. Human communication is so cerebral and nuanced that it’s impossible to give catch-all answers, and those that do quickly hit a wall of how useful their advice can be.

So how do we deal with this issue?

How To Learn Dating By Getting General Advice

If you’ve ever spent much time looking at relationship and dating advice content, you’ll notice that one of two things occur. Firstly, we see sweeping judgements being made that clearly don’t apply to everyone. Content creators and advisors will put out ridiculous statements like ‘all men are capable of cheating’ or ‘all women like it when you don’t take no for an answer’.

You run into a lot of issues very quickly when you form advice off limited personal experience, and those issues compound when you try to teach others these things as lessons.

Secondly, to avoid the first problem, people tend to get super specific. “So you should absolutely avoid pulling out chairs for women under 5’4 with brown hair that were born between May and August”. For the all of three people that will ever run into this scenario in their life, they may find this kind of content (“6 Tips On How To Date Using Mental Hacks…” or other similar nonsense) useful. But it still doesn’t actually infer any practical advisory value to the 99.9% of people that are likely to see it.

This is because of a incredibly easily overlooked discrepancy between how we talk about dating versus how to date people in real life.

Like it or not, we date (and learn how to date) one on one. There are some very, very rare exceptions in the poly community, but for the vast majority of people, how we date tends to be across a table from an almost-stranger. And if you’ve ever done any science or statistics courses, you’ll know that a sample size of one leads to a lot of issues with consistency.

Dating Just ‘One’ Person

When we go on a date with a single person, we have to try and take all the advice we were given, by multiple people, produced from an amalgamation of multiple experiences, and directed at an audience to be consumed in multiple ways, from multiple perspectives. We combat the sample size problem by speaking generally, about dating patterns and habits. We talk about demographics of people as if they’re all made to match, with identifiable traits and patterns that we can rely on to give ourselves an edge.

Obviously, this doesn’t really make sense. Humans are too unique, and stereotyping very rarely has practical value when the person across from you is a living breathing human being with experiences and individual characteristics.

This is where the issue with receiving dating advice comes in. Very few people have the ability to bridge the gap between generalising with advice, and figuring out how to date by utilising it with an actual partner. Sure, I know that the internet says that all redheads are more energetic and extroverted, so why is this delightful strawberry-blonde in front of me remarkably shy and timid.

We base our behaviour or our prejudices on what limited generalisations we’re able to make, because there isn’t a dating cheat sheet that works person-to-person. I can’t go on a date and use advice I found on Reddit to prepare the same way for each person each time.

Being Flexible

A man sitting on the ground flexibly holding posture - symbolising how to date flexibly

So what do we do then?

Getting advice is useless, I hear you cry. What’s the point of this dumb website then? Well, fear not, because there is an answer, and it’s pretty straightforward.

It doesn’t involve complaining about dating advice on reddit.

We must simply learn how to date by being flexible.

Dating advice isn’t actually an instruction manual. It’s the background knowledge that is never going to be asked about in the exam, but is required as a foundation to understand any of the exam material. The dating equivalent of the people that memorised the answers and simply parroted them back onto the paper are called pick-up artists. That’s why these people are creepy. They provide sweeping advice as if it works on every single person every time, have little to no interest in foundational social intelligence, and struggle immediately when their scripted lines fail or lead somewhere unexpected.

You can’t learn to cook by reading recipes. You have to try each ingredient, learn what combination makes what flavour, understand the fundamental elements like heat, seasoning and time, and how to modify each to change the outcome.

How we date is the same exact process. I can know that traditionally-oriented women like chivalrous gestures, and I can memorise a couple to prepare beforehand, but if I see that the girl I’m actually talking to is seeking some independence despite being from a conservative background, it makes sense not to undermine her by running ahead of her to open a door.

The barrier to entry for these situations is figuring out how to transition your general advice into specific advice based on what you can see in front of you. Body language, context, reactions to certain things, the actual words that your date literally tells you, all of these are clues on how to twist what you know to best suit the other person.

Because we’re not just trying to hit a tennis ball.

We’re trying to find the right racquet to pair with the correct ball, and connect with it in just the right way so that the ball wants to bounce back to us for a second go.

And if that all sounds like too much work, then I suspect you and I both know the reason your last few dates didn’t quite work out so hot.

For some general advice you can use as practice – here’s an article on how to think about a first date.


Why can’t dating advice be straightforward?

Unlike sports coaching, where there’s a clear objective (such as hitting a tennis ball correctly), dating lacks non-negotiable fundamentals that apply universally. The nuances and complexities of human communication and interaction make it challenging to provide one-size-fits-all advice. Teaching someone to avoid extreme faux pas is simple, but the subtler aspects of connecting with another person on a date can’t be boiled down to straightforward advice that works for everyone.

What are the problems with how dating advice is generally given?

Dating advice often falls into two problematic categories: making sweeping judgments that can’t possibly apply to everyone or being overly specific to the point of irrelevance for most people. These approaches fail because they overlook the critical difference between discussing dating in general terms and the reality of dating, which is an individual experience with a unique person each time. Generalizations and stereotypes rarely offer practical value in the deeply personal and variable context of a date.

How can one effectively learn how to date despite the limitations of general dating advice?

The key to learning how to date effectively lies in flexibility and the ability to adapt general advice to specific situations. Dating advice should be viewed as foundational knowledge, not a direct instruction manual. Successful dating involves observing and responding to the unique individual you’re with, such as their body language, verbal cues, and personal preferences, rather than relying on memorized strategies. It’s about finding a balance and connection unique to each interaction, much like pairing the right racquet with the correct ball in tennis.

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Cain Parish

Cain Parish is the owner of A prolific writer, educator and relationship coach since 2019, he specializes in dating, relationships, emotional intelligence and social skills. He is also the author and creator of the world’s largest and most comprehensive database for dating and relationship advice, which can be found on his website. His first book, I’m Sorry I Egged Your House, is due to be published in 2024.

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