Ultimate Guide to Dating Part 1 – Having Fun and Building Relationships

Having fun and building relationships through dating

Phew! She just said YES.

Well, to going out on a date with you at least.

So now it’s time to start planning your first date. How exactly are you gonna sweep her off her feet and into your bed?

If you’re new to dating, you’re probably thinking, “Surely if me and her are compatible, our dates and happily ever after will just work out, right?”


The sad fact is that there are many men and women who should be together based on their compatibility… But their first date SUCKED, and therefore they’ll never see each other again.

Think about your most recent dates for a moment.  Have you ever been on a date and you thought ‘we should totally be together’, but then the chemistry just fizzled out, or there was no follow up date?

This happens ALL THE TIME. And it’s not too surprising either.

First dates are inherently nerve-racking and totally awkward! You’ve never met each other or you’ve never met like this before, and now you’re both trying really hard to seem  normal, relaxed, and not freaked out.

What’s worse, if you really like the woman you’re with and you’re distracted by her beauty, then you’re under even more pressure to impress. You might accidentally say or do something stupid, just out of nerves or because you’re not thinking straight. And before you know it, you’ve just blown it and there’s no turning back.

That’s life, my friend. And that is the world of dating.

You don’t get a second chance to make a first impression. And when there’s pressure to perform, it’s pretty easy to fuck things up. Essentially, that’s the newbie dating experience in a nutshell.

But you can stack the odds of success HEAVILY in your favor by knowing, applying and practicing strategies that help you date well.  And that’s what this article is all about.

Guys who know how to date well consistently have successful dates and get to have their pick of the women they date. I’m one of those guys and I coach guys in how to do this and achieve the same results.

If I’ve made the effort of meeting a girl, arranging a date with her and then allotting precious time to take her on a date, then I expect the date to go well!  Meaning that if I like the woman I’m dating, I want to make sure that by the end of the date, she likes me (A LOT) and wants to see me again. It’s seems like common sense to me.

The trick to having consistently successful dates is knowing:

  1. How to have fun and enjoy the date
  2. How to build a relationship with your date
  3. How to plan and run kick-ass dates

This is the stuff that great daters know VERY well. They typically acquire this knowledge through trial error and error, and by learning the hard way (like I did).  Or, if they’re lucky, they might stumble across some insightful and practical wisdom like this article. Like you just did. Lucky you!

By the end of this article and the next in the series, you’ll know all the stuff that great daters are in the know about, you just need to go out, apply it and practice it on your dates. And that’s the fun part!

1. How to have fun and enjoy your date

Having fun on a date is ABSOLUTELY CRUCIAL, especially if it’s your first date.  If your first date and time together isn’t enjoyable, then don’t expect a second date.

Think about it for a moment, when you hang out with your friends, you hang out to have fun and enjoy each others’ company, right?

Then why would a first date, or any date for that matter, be any different?

When it comes to having a good time, the same applies when you’re on a date, in fact you should try to be even more fun, like the MOST fun and playful version of yourself.

The reason that you have to turn the fun up a little is that you don’t have a lot of time to make a first impression, probably only a few minutes, right at the start of your date, before she decides whether she actually likes you or not.

If you want to know how to make your dates more fun, here’s a great article to get you started.

2. How to build a relationship with your date

Whether you’re looking for a quick hook-up, a happily ever after, or anything in between, there are three stages to building a relationship that you must go through on ANY and ALL dates, in order for them to be successful.

Not understanding these relationship stages or building them in the incorrect sequence is a fundamental stumbling block that most people get wrong from the very start of a date.

So what are these 3 stages?

  1. Building attraction;
  2. Building a connection; and finally
  3. Building sexual intimacy

In DateSchool, we often refer to Attraction, Connection and Sexual Intimacy as the three pillars of all relationships. These pillars need to be built (to some degree) if any kind of sexual and loving relationship with a woman is to happen. Whether you’re looking for a girlfriend, a one-night stand or a lifelong soulmate – you have to build attraction, connection and sexual intimacy, and in that exact order.

Understanding these relationship pillars is fundamental to dating well, so if you’re not already familiar with them,

Here’s a quick overview:

1. Attraction

When it comes to kick ass dates, attraction is of utmost importance.

Attraction is the overpowering feeling that you get naturally when you meet someone that completely BLOWS YOUR MIND with their inner and outer beauty.

Your heart races when they’re nearby. Your nerves go into overdrive. You can’t take your eyes off of them, but you’re too nervous to look them in the eye or hold their gaze for too long.

This is attraction. It’s that natural gut-feeling, which hijacks your thoughts and emotions, and urges you to feel obsessed about the hottie in front of you.

Put another way:

“Attraction can provide a link to another human so irresistible that it feels like an enchantment, one that renders all other needs and duties oddly meaningless, tiresome and irrelevant.” 
– Deborah Orr, the Independent


Attraction is as important as fun, when it comes to successful first dates.  In fact, they’re both the key ingredients in the DateSchool first date equation:



If you haven’t had fun or built attraction on your first date, there simply won’t be a second date.

Or, if you have fun on your date but don’t build attraction, she’ll probably describe your date to her friends like this:

“Yeah, he was a nice guy, and I liked him as a friend, but there was no real chemistry.”


By contrast, you want to be the guy that MAKES IT RAIN chemistry! You want to be drenching the women you date with raw chemistry and irresistible natural attraction! That’s your first and #1 goal when you first start dating any women.

There’s an entire masterclass devoted to helping you nail the art of building attraction, including a seriously effective crash course in how to become your most attractive naturally.  And to give you a taste of what that’s all about check out this introductory article to help get you started building attraction on your dates now.

Once you’ve successfully built attraction with her and you know for sure that she feels attracted to you, then you can switch gears and start building a connection.

2. Connection

Connection is that feeling of true companionship that we look for in our soulmates. It’s all about understanding and appreciating each other. Connection is built over time through shared experiences, feelings and memories.

“It is not a lack of love, but a lack of friendship that makes unhappy marriages.” 
– Friedrich Nietzsche


Unlike Attraction, which is mostly driven by immediate primal and physical urges, connection is a warm sense of friendship and companionship that’s deeply psychological in nature.

“Physical attractions are common, but a real mental connection is rare. If you find it, hold onto it.” 
– Anonymous


Connecting with someone is all about getting to know them as a person, understanding them and getting in sync with them, so that you can grow to trust, appreciate and really enjoy each other’s company over the long-term.

It can take a few hours or even days to build a deep and strong connection with your date, but it’s definitely worth investing the effort for two reasons:

  • You might end up really liking each other and falling crazy in love, which is awesome!
  • Most women need to feel a certain amount of connection before they’ll feel comfortable enough to sleep with you. So even if you’re just looking to get laid, you’re going to need to build a sufficient amount of connection first.

Building a connection is about spending time talking with her so that she feels like she really knows you, understands you and can begin to trust you. This is a key to kick ass dates. Key.

The more connection she feels, the more she’ll grow comfortable with the idea of getting sexual with you, provided you’ve built enough attraction first! I can’t stress that enough.

How to build a connection with your date

You build connection with your date through deep conversation and by making an undistracted effort to genuinely get to know her for the person she really is.

“All a girl really wants is for a guy to prove to her that they are not all the same.” 
– Marilyn Monroe


From the outside, it looks like you’re paying her undivided attention; as if she’s the most interesting person in the world.

“The most desired gift of love is not diamonds or roses or chocolate. It is focused attention. Attention says,  ‘I value you enough to give you my most precious asset — my time.’”
Rick Warren


The quality and depth of your conversation when you’re building a connection is different from the playful and flirtatious attraction-building stage of your date.  To build a connection with her you want to really understand what makes her tick and show your appreciation and liking for what you’re hearing.  This is the kind of stuff that you’ll want to learn about her:

  • How she sees herself and how she wants the world to see her
  • What’s important to her and (equally) what’s unimportant
  • What she enjoys doing and why
  • Not just where she lives, but why she lives where she does
  • Not just what she does for work, but how she feels about it and why she got into that line of work in the first place

The last three examples in the above list highlight a key concept for building a connection – you really want to understand her “why.” What motivates her and makes her tick?

There are loads of other great questions like this which help make your conversations more deep and interesting – here are a few of my favourites:

  • What’s the favourite thing that you own and why?
  • Who’s your best friend – what makes them special?
  • What’s the kindest thing that you’ve ever done for someone else?
  • What’s the most embarrassing thing that’s happened to you this year?
  • If you were going to take me away for the weekend, where would we go?

Using deep questions like this to build connection is common practice among daters who have their shit together. All the best pick-up artists and date coaches have their favourite questions that they like to ask. These help them to build connection and even qualify women; i.e. distinguish whether or not the woman they’re speaking to has the substance and personality that’s worthy of their time.

Studies have even shown that asking and answering deeply personal questions is a short-cut to building deep and powerful connection quickly.  One study in the US showed that by asking each other a specific list of questions for 45 mins, couples who had never met before became closely bonded.  Even two months after the experiment, about a third of these couples had hung out and/or sat next to each other in class afterwards!

If you want to know the actual questions that were used in the experiment described above, I’ve pulled them together with some instructions for you in this one helpful PDF, which you can save in your phone, so that it’s nice and handy for your next date.

If you’re looking to mix it up or personalize your own set of date questions, then you can draw on this book, The Book of Fabulous Questions, for inspiration, which is one of my old trusted favourites. I use questions from this all the time and because it’s pocket sized and fun, I’ve even taken it out on dates before, when I was being too lazy to memorize the questions that I liked. It’s the perfect conversation catalyst.

Hopefully this all helps to paint a picture of what I mean by building a connection, through asking questions.  It’s about:

  • Understanding her and then showing appreciation and liking her for the person that she really is; and
  • Revealing personal information that you wouldn’t normally share in more casual conversation

You’ll know once you’ve built strong enough attraction and connection with her because as you get closer to her, she’ll begin to respond more warmly to your touches.  She’ll even touch you back and try to get closer to you.

As you’re doing this, you’re already starting to build sexual tension and intimacy, which is the third and final pillar of building a relationship with your date.

3.      Building Sexual Intimacy

When you’re building sexual intimacy with your date, things really start to heat up and get a bit sexy and intense. This is when seduction begins.  And if done well, sex can soon follow.

For most guys, this is the stage of the relationship that can’t come fast enough.  Newbie daters are always asking me, “When do I kiss her?” and “When am I supposed to make a move on her?” Way too many guys try to jump into seduction, like it’s some kind of surprise.

But you can’t rush into sexual intimacy.  She has to feel ready for, and comfortable with, your seduction, if you are to succeed.  This means you need to have built up enough attraction and connection with her beforehand.

A general rule of thumb is that it takes roughly 7 hours of interaction (in person and/or on the phone) time to build up enough attraction and connection for sexual intimacy to be welcomed and encouraged.  Of course the actual interaction time varies depending on how skilled a dater you are and how prudish or promiscuous your date is.

You’ll know that you’ve built up enough attraction and connection and that she’s ready for sexual intimacy and seduction because these kind of things start happening:

  • As you move closer to her, she doesn’t back away, or even better moves in closer to you
  • As you touch her, she doesn’t recoil and she starts touching you more
  • The intensity of your eye contact increases; as you start looking at each other more deeply and for longer periods, without saying anything
  • As you look at her lips, she looks at your lips too
How to build sexual intimacy with your date

The guiding principle for building sexual intimacy with your date is to build SEXUAL MOMENTUM smoothly and seamlessly, as opposed to awkwardly and jerkily.

This means gradually increasing the intensity and intimacy of your touches, keeping pace with how much she seems to be encouraging you.  This does not mean surprising her by diving in for a kiss completely out to the blue.  The standard sequence looks like this:

1.      Platonic touches – Social in nature – the kind of touches you’d do with anyone e.g. shake hands, pat on the shoulder, etc.

2.      Playful touches – More personal in nature – the kind you’d do with your kid sister, niece or nephew who you are close to – e.g. playfully push them, tickle them, elbow them in the side

3.      Sexual touches – Much more intimate in nature and can be anything from holding hands, to locking lips or getting down and dirty.


The BIGGEST mistake that a lot of guys make when trying to seduce women and go in for the first kiss or attempt to seduce their date prematurely, is that they don’t do enough touching beforehand to create and then build sexual momentum.

This is how most guys get shut down. They try to move too fast without building things up, and this often leads to last minute resistance to their advances.

If your seduction efforts are to be successful, her body must feel comfortable with your touch and be receptive to it. Escalating the intensity of your touches steadily and smoothly, in response to her feedback and encouragement will help build sexual momentum with her at a natural pace, and it will also ensure that seduction is something that you both want.

Building relationships – your action plan

Smart daters use their dates to deliberately and systematically build relationships.

Taking this approach guarantees that in the shortest possible time, women will feel:

  • Powerfully attracted to you;
  • Deeply connected and bonded with you; and
  • Truly ready and desiring to be seduced by you.

This is the approach by which you can make a woman feel “swept off her feet” and as if she’s fallen “head over heels” for you, naturally and powerfully.

The important lesson here is to not go into your dates with the vague intention of getting to know each other or just seeing what happens or playing it by ear.

Instead, take the lead in building the relationship with direction and this method to ensure consistent success on your dates and minimize the wasted efforts and chances with women.

I know this might sound overwhelming at first, but the way to get naturally good at building relationships is to focus on small steps. You need to practice building each relationship pillar separately (in order) and then move onto the next.

Following this approach means you will:

1. Get good at building attraction first

a.     Work to become the most attractive version of yourself and bring that version of yourself to your dates.

b.     Become practiced and polished at conveying your attractive qualities quickly and powerfully with the women you date. This will ensure that you create a strong and attractive first impression every time.

c.     Have fun, be playful and enjoy yourself!

2. Then focus on building a connection

a.      Engage her in a deep conversation, which will allow you both to reveal more information about who you really are and what makes you both tick.

b.      Have some standard questions ready which will prompt some level of disclosure and keep the conversation interesting.

c.       Pay her undivided attention and get in the practice of showing your appreciation for her uniqueness, through what you compliment her on both verbally and non-verbally.

3.  Work on seduction and building sexual intimacy

a.      Give thought to your surroundings to ensure that you’re in a private or isolated place where you won’t be interrupted by people around you.

b.      Practice escalating the intimacy of your touching.

c.       Practice triangular gazing and going in to kiss her.

d.      Practice building sexual tension and momentum in your foreplay.

Following this step by step approach and learning how to establish and build the relationship pillars in the right order is vital to overall dating success. And please know that you will likely become better in some areas than others (e.g. you can build attraction but are really awkward at creating a deeper connection).

Realize that this is ok. In fact, it’s even better than ok!

It’s helpful that by nailing down how to build attraction, you’ll soon build a pipeline of women who feel attracted to you, not just on dates, but amongst your female friends, in your social networks or even at work.  These are all perfect candidates for you to start practicing your connection and seduction skills with.

It typically takes most guys three or four dates with different women to start seeing the relationship pillars develop in their dates and to start naturally thinking about relationship building in this way.

Once this happens to you, you’ll be blown away by how much of a positive impact it will have on your dating.  Having this perspective about relationships and being able to diagnose at any time which pillar needs to be built more strongly will give you a HUGE advantage in bonding quickly and sexually with every woman that you interact with.

It’ll drive a step-change in your success with women and you’ll never look back.

What remains then is to start deliberately planning your dates so that they are more conducive to building attraction, connection and sexual intimacy by design.

We’ll describe exactly how to design your dates this way in the second part of this Ultimate Dating Guide series.