The Perfect First Date


We seem to be living in an age where dating has become a complicated mess for many people.

From what the older generation tells me, it used to be a lot simpler. Aunt Whoever would get you to take her friend’s daughter to the local disco, and 12 months later you would marry her. Done and dusted.

Of course, that generation has been the worst in history for divorce rates. Go figure.

These days, not only has dating become a messy and mostly online experience, it’s still fraught with the irrational pressure to find “the one”. This leads people to put on a fake persona while they grill their dates for compatibility information. Not exactly the most fun experience.

Then we have online dating, and the whole process of trying to use someone’s carefully crafted (aka completely bullshit) profile to figure out if they’re worth spending our precious time with. That’s followed by the hit-and-miss trail-by-fire of dating these mysterious strangers one at a time. Whew!

And what seems to be missing from all of this is fun, excitement and integrity. So we Brojo boys got together and pooled our thoughts about how to make dating a more enjoyable experience for all involved. This applies to both guys and girls, gay and straight. Have a read and comment below with your thoughts.


Let’s start be redefining what dating is all about. Instead of dating being about Finding The One or getting laid, let’s try and reframe it as something more healthy, enjoyable and based in confidence rather than neediness.

Ultimately dating is no different from any other interaction, and a ‘first date’ is merely another interaction with a person. Like all confident interactions, what you’re really measuring at first is whether or not you will be a good fit with each other. As we’ll discuss later, this is NOT about analysing them to see if they fit your long list of criteria. Instead it’s about whether or not you will enjoy each other’s honest company, due to sharing the same values in life.

First dates should really be about going out and having fun. If you’re not enjoying it then there’s really no point. A great way to make dating fun is to see it as a chance to practice social skills and confidence. You might practice being more open and vulnerable, or more playful, or more directly bold. If you’re out practicing your skills, you’ll find your attachment to external outcomes (e.g. sex and marriage) will fade, allowing you to just enjoy the date itself.

Dating is a chance to establish boundaries for the potential longer-term connection (note: we use the word ‘connection’ instead of ‘relationship’ to break away from the rules we have attached to the word relationship). If this person is going to be a bad fit for you, it’s best to figure this out early.

In the end, a healthy first date is about one thing only: to enjoy a new connection, for however long it lasts, even if it’s only this one date


Some guys come to me for coaching because they often ruin dating by going into it with all sorts of unhelpful mindsets, which we’ll discuss in more detail soon. For now, here are some helpful mindset practices the Brojo crew recommend:

Have nothing to prove, be there for You. You’re going to have fun with or without them – it shouldn’t even really matter if they don’t show up. Remind yourself that you are just going to see what they are like, and use the date to figure out if you want to see them just one more time (forget long term).

Aim to judge them on whether or not they share your values (e.g. are they honest? Do they like to get out of their comfort zone?), rather than some superficial list of characteristics (e.g. must have a good job and love kids).

Be open to them surprising you. Maybe they’re not your usual type, but maybe they will redefine your type! If you think they are already ‘something’ before you meet them, your mind will be closed to alternative possibilities. They will feel this and shut down.

Remember that you are inviting them to your world. You absolutely should NOT be changing your world to suit them on a first date. They haven’t earned that level of investment yet. One way to manage this is to start ‘dating yourself’. Take yourself out to fun events every week, and along the way you can invite people to join you, rather than setting up a new ‘date’ just for them.


Most dating dies before it even had a chance to live. Check out this list of common dating errors.

1) Trying to prove yourself and impress the other person (gives you lower status which makes you unattractive). If they’re a good fit, you won’t have to try.

2) Sticking to traditional rules like ‘dinner and a movie’ or ‘wait til the end of the date to kiss them’ and ‘the man should pay’, rather than creating your own rules based on your unique values. Or even better; having no rules and allowing the connection to grow uniquely between the two of you.

3) Believing the first date is the start of a relationship, and becoming attached to that outcome. Neediness is about as attractive as pedophilia. If your dates often flake on you after the first time, it’s most likely due to neediness. And yes, they can still be put off you when they’re needy too, we’re all blind to our biggest faults most of the time.

4) Trying to get laid (as opposed to naturally escalating sexually if it feels right). Having an agenda before you get started is so obvious you may as well have it written on your forehead. This makes the other person feel like they’re being scammed. If you want to fuck someone, then just tell them that instead of the rigmarole of a formal date. Casual sex is what nightclubs and parties are for. Dating is for connection.

5) Failing to set boundaries for fear of scaring them away. Most people call this “getting to know each other”, which is coward-speak for “I’m too afraid of them not liking me to be honest with them”. When you don’t set boundaries the other person will not know how to work with you, and this will make them feel unsafe. They’d rather get told off for crossing the line than be left wondering what you really think of them.

Standing up for yourself makes people trust you and helps weed out people who don’t respect you. If you don’t do it on the first date, odds are you’re the kind of person who never really does it properly. Break the pattern!

6) Lying and hiding the truth about yourself. Believing you have to keep it ‘positive’ and make them ‘happy’ – based on a fear of being seen as ‘weak’ for having normal human flaws and insecurities. This can be represented by constantly checking up on them – “Are you OK?” – or refusing to share insecurities. When you have a smooth polished presentation it just tells the other person that you’re not comfortable with them. Trying to keep it smooth and comfortable just makes them wonder what you’re hiding (unless they’re really naive and think you’re genuinely without flaws).

7) Trying to think of something ‘good’ to say, instead of just being curious and commenting honestly on what you observe. You will never run out of genuine and interesting things to say if you’re actually paying attention. Listen to what they say and wait to respond. Allow yourself to observe what is happening. There’s plenty going on.


Spontaneity is what happens when you let go of having an outcome-driven plan and just start mixing it up and having fun. Going on an impulsive adventure together is the best date anyone could ask for. Different locations, unusual events, impulsive decisions – these are all great logistical factors.

Leadership is important, particularly if you were the one initiating the date. You can’t ask someone out and then hope they lead the thing. By taking charge of investment levels, location and logistics, physical escalation, and all other risk-taking, you set yourself up to be the leader in the relationship. That said, be sure to balance investment, they should also take turns at leading, e.g. “Alright, I chose the venue so you choose the drinks!” Be decisive – it’s better to get it hilariously wrong than to be constantly asking “So what do you want to do now?”

On that note, balanced investment is crucial to a healthy first date. You can lead but do not significantly invest more than they do. Nor should you allow them to invest more than you. Levels of intimacy, honesty and respect must be equal for a value-based connection to grow. How you act on the first date will serve as a precedent for your entire relationship with this person. Get it right from the start and you won’t have to fix anything later.

Believe it or not, people connect deeply on shared insecurities. When I eavesdrop on first dates (a hobby of mine), I often hear each person only talking themselves up, highlighting good times and saying nothing about the shitty times. Yet people bond on shared sorrow. We connect with the rough parts, not the smooth. Next time you’re on a date, tell them something you don’t want to admit. It won’t guarantee they like you, but it will guarantee that if they are a good fit they will be given the chance to connect with you genuinely.

When you’re vulnerable and honest you create an emotional ride of highs and lows. Most people prefer this to boringly smooth. There’s nothing wrong with disagreements and the odd awkward silence. You’re much more memorable and interesting if you create a range of experiences, which will occur naturally when you’re as honest as possible. You don’t need to fake or manipulate any of this. Try to be so honest that it drives them away – this is how you find the greatest fits. If you’re not sure what it means to be honest, read this.

Can we talk about honest sexual escalation? If you want to kiss your date, then try to kiss them, don’t wait for some rule or signal. Allow minor ‘rejections’ to happen, as they will help you measure where the different investment levels are. This doesn’t mean push past reasonable consent, but understand that “No” usually means “Not yet” (unless they leave completely). If you don’t touch them when you want to touch them, you risk them thinking you don’t find them attractive. If you wait to follow the rules, then you’ll be remembered as being the same as every other person they’ve dated.

Congruence and integrity are key; are you treating them any different to how you treat your friends and family? Be You, as if you have nothing to lose. They have been invited to your world; let them decide if they want to stay, instead of trying to make them want to. There’s nothing wrong with being polite and treating them nicely, provided this is how you treat everyone. A first date should not get special treatment, particularly if this is not how you’d act long-term. Act as if they are already a long-term friend or partner – actually, if you treat every stranger this way, your social circle will expand immensely, pretty much guaranteed!

Indulge in silence, and plenty of it. Most people avoid silence on a date, which actually makes it more uncomfortable. Friends are OK being silent around each other, it shows comfort. Get started early on this to escalate rapport building (or to bring a bad-fit connection to an end quickly). Allow yourself to contemplate before you respond, and let them contemplate before they do. Silence builds rapport more than talking, as long as you are OK with it. Forced conversation to fill the gap is needy, shallow and often quite fake.

And as a final tip, use statements instead of questions. If you are going to ask a question, make sure you genuinely give a shit about the answer first, don’t do it just to keep them talking

Check out this article for more great tips from experience coaches, dating experts and lifestyle guides:


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