Finally the End of Shitty Dates

Happy (belated) Canada Day Everyone!

Last night during IDI3, a few of us were breaking down our favorite dates and the thought process we work under in forming them.

(IDI stands for “Ideas Developing Ideas; A Kingpin Social Idea”. It’s a weekly event that Kevin and I run where we invite 8 other guests to come hang out with us. The concept is that we will just sit around, talk, smoke sheesha, and discuss ideas… but with a focus on digging deeper to develop these ideas, using a “higher” level of thinking.)

Obviously being involved in pick-up for so many years, the thought process I work under when I go on actual dates is on the same lines as traditional game theory:

– Bring her into your world
– Bring her to places you know people for “social proof”
– Keep it casual, playful and fun

… all of which being great concepts to use.

But there’s one flaw in the system, which I will get to later. (HA!)

Before I got into pick-up, I actually loved going on dates. I would just wing it and go on a date that would be fun and unique for both of us. The night wasn’t intended to be “special” but it always ended up being awesome, because the night was focused on the two of us doing things we enjoy, and doing them together, instead of running through a pre-planned date built to communicate a bunch of qualities I have already, that I don’t even need to communicate.

See this is an issue with so much of the old school theory: it doesn’t scale as well as it should. Here’s an example:

I was talking with one of the guys, and he likes to hang out at restaurants and lounges. This is something he does every night, so naturally because he’s a social guy, he knows a ton of people at every venue too.

On a typical date he will bring the girl with him to go for drinks at a bunch of different lounges and restaurants. Good idea right? Of course. By doing this he is bringing her into his world, doing an activity he would be doing regardless of having the date or not, while also showing this girl that he knows a lot of people, giving him that social proof and “demonstrating higher value”.

But what’s wrong with this?

He’s already a cool mother fucker. Taking the girl out like this is alright, but my buddy is already a cool, high value guy. So this actually ends up doing more harm than good. The girl ends up getting a player vibe, and he has to deal with a ton of bullshit from every girl because of it. (He used to work in the industry, so he has a bunch of those stereotypes on him already.)

Is he a player? Not at all. And I find there’s nothing more annoying than having to deal with bullshit like this from girls when it’s just not true at all. It’s a tough battle to have, and starts the relationship off on the wrong foot.

Not only that, but if he’s running into a ton of people he knows, that is taking time away from him and her actually interacting, having fun together and connecting. The date isn’t “special”, and neither of them will leave with a feeling of that “spark”. More likely they will leave with a feeling of “that was kind of fun, I’d do it again but it wasn’t the most amazing time of my life.”

Or maybe that’s just my opinion from my experiences.

Now take this with a grain of salt. I’m not suggesting you never do a typical date, or that you ignore these concepts that are very beneficial to work with. The difference is, if you are already a cool guy, you might not need it.

I’m sure if my buddy went on a date with that same girl where it felt like they were the only two people that existed in the world, where he could give her his full attention and vice versa, where they got to know each other in environments they enjoy, the connection would be that much stronger.

Some people might say they would only do this if they were actually interested in the girl. And I would agree. But I would also say that if you are going on dates with girls you aren’t interested in, you are being a fool. Why waste either of your time? I know I have better things to do, and I’m sure she does too.

The only time I would recommend going on a date with a girl you might not be that interested in is when you haven’t been on very many dates and are still working on learning to connect with people. There’s a good chance that you might not be interested yet because you just don’t have that connection, but if you aren’t very good at connecting with people quickly, going on a date might be the time you need to get to know each other and form that connection. Just something to think about.

Some people might also say that going on a “special” date with a girl you actually like would be bad because you are treating them differently than other girls. And to that I say you’re an idiot, because it has nothing to do with that, nor does that matter at all.

So how should you actually think about dates?

Instead of thinking on the lines of “what activities do I do already that I could bring her on”, think about the activities you do already and what the reason is that you like them. For example, if you put on a weekly get together with friends where you play Frisbee outside in the sun, you could invite her to that… OR you could think about the reason you are playing Frisbee outdoors every week and form a unique date along those lines instead. The most likely reason you play Frisbee every week is because you like being outdoors, in nature, doing something physical, being active, getting out of your house.

So apply that concept and make a new date that is unique and special, a date you will enjoy that much more where you can give each other the attention you deserve.

With that example in mind, instead of bringing her to your weekly Frisbee event, you could plan a day to go hiking together. Hiking is outdoors, active, in nature. It’s all the same things, except it’s unique and special for the two of you, where you can give each other your full attention and actually have an experience together.

Or maybe I’ve just been smoking crack.

When you do a date like this, it will be fun for both of you, which is what you guys want to be connecting on early in your relationship.

“Do you guys actually have fun together?”

So what is my all-time favorite date?

Ice-skating. This isn’t super original or anything, but I actually enjoy it a lot. I played hockey for 15 years, so when I get on the ice she will see a very pure and congruent side of me. There are few places I enjoy more than being on the ice. Now while we skate around we can talk and connect, but also have fun, be playful, and most likely hold hands. It’s cute, it’s corny, but fuck it. These are things I enjoy.

When I go ice-skating with a girl I’m interested in, it doesn’t matter if I have “social proof” or not. She doesn’t care about that shit. If she was willing to come on a date with me, she probably thinks I’m a cool interesting guy, so as long as I’m congruent to that (which will be obvious as she hangs out with me skating around on the ice, where she will be able to see how happy and passionate I am), everything will be fine. No old school game theory needed. And I’m not going to end up shooting myself in the foot because she gets a player vibe.

From the very start of our relationship it can grow at a natural normal pace. Every girl I’ve ever dated as begun that way, with dates that ended up being unique adventures instead of the same old activities I do all the time.

So what is the flaw to old school pick-up theory when it comes to dates?

It lacks inspiration.

And that’s the big reason why for quite some time going on dates has been a painful process, one where I’d honestly rather stay home and work on the business or go DJ with friends. I lacked inspiration, because my mindset was coming from that pick-up angle, instead of going on a special unique date with a girl I dig…

… where the possibilities are endless…

… and it might actually be a time you never forget…

Hope that helps.

If it did please share this with your friends. Also comment and let me know what your favorite dates are. Let’s share these awesome ideas with each other so we can all grow as one.


PS. If you are a bit less experienced and are having trouble turning your numbers into dates, check out this amazing post by Brian.

PPS. It was really cool how a bunch of you guys added me on Facebook and Twitter after the last post I made. If you haven’t already, add me. I’ll help you out, seriously. No strings attached.


  1. I really like the idea of Ice Skating Date these are the dates where both people enjoy, having fun, having some laughs together after cracking some jokes. Other than that I really like something that we can sit down at nice restaurant/bar/pub or even similar to Ice Skating is walking around the city park (Ex: Fish Creek). Maybe even a picnic during the hot summer days – may sound a bit old school but hey, maybe someone likes it – I wouldn’t mind! That’s it for now!


  2. Hey Max.

    Thanks for responding! One of the other ones I do a lot is walking through Princess Island Park. You can stop and play frisbee for a bit, sit on a bench and talk, bring food for a picnic, etc. The key is to make the date something “special” so you can actually connect and experience something together. Shared experiences is how you bond; build connection.

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