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This is a draft that will take a few iterations. Lots of issues.

"Give that chick a high five! Sounds pretty simple, right? But for beginners..."
Who are you writing it for?
- most people reading GC are beginners. Furthermore, people surprised at the difficulty of the exercise are definitely beginners. Yet everyone is liable to assume that you are talking about somebody else. Better: "But it can be a challenge and a great way..."
- non-beginners already know that the exercise can be difficult, so they don't need this explanation.

"They say what doesn't kill you makes you stronger. That's one reason why learning game is so hard." --- wrong. It makes learning game easier. If what doesn't kill you made you WEAKER, then learning game would've been immeasurably harder.

"If you are so embarrassed or so worried about social fear that you can't even give someone a high five..." --- yet the article goes on to argue just how hard and how useful it is. If most men enrolled in a pickup bootcamp fail to complete the exercise on the first try or even on the first day, not to mention all the other men and all women, that makes it an extremely hard standard. So if you cannot do it, then you give some fucks and could give less, but it's hardly "way too many".

"...you might not want to stage this game near a playground." --- that's a tasteless joke that is completely out of context; it does not add anything to the article. After all, why would you be practicing and getting high fives on the playground to begin with?

"How far can you run?" --- the following paragraph does not really answer that, so the title appears out of context.

"You are not that different or special" -- granted, and you may also assume that tomorrow you will have a lot more time and willpower, and that you are more compassionate than the average person... the list of biases goes on and on. Why bring up this particular bias?

"If you are afraid of what people think when you approach women, they you're going to suck at game." --- yet just about everyone is afraid of it, including many guys who are good at game.

"The point is not just to get a high five, but to solve a problem of how to get one." --- the point is neither, it's just an exercise. Perhaps the author meant that the value lies in learning to approach game as problem-solving, learning to be creative. Yet I disagree: it is the anxiety that kills creativity, much like most guys know what they can say on an approach, they just can't think of a line they are comfortable saying. In a perfectly comfortable environment, most people would have no problem racking up high-fives.

"Often it's not what you say, but how you say it." --- how is it relevant? The article was not discussing trying to get any results.

"My wife dead..." --- how is that funny?

"If you want to be an amazing day gamer, you have to silence that little voice..." --- but you can't silence the voice. Meditation traditions and modern research on willpower both agree that the key is not attaching to the voice, letting it be (and taking action anyway), and not trying to silence it, which can be counterproductive.

"Your approach anxiety will decrease: as soon as the clock starts, the adrenaline spikes." ---
that makes no sense. An adrenaline spike should increase anxiety, not decrease it.

"But maybe you don't want to just be good at day game, but excellent." --- yet the article positioned this as an exercise for beginners.

Here are some other (difficult) exercises that I've personally found useful:
- High five - low five - fist bump. It's funny, just how many people would agree to a high five, but not to a low five, or would do a low five, but decide that a fist bump is too much.
- High five exercise without speaking.
- Giving money away to a random woman. You can use $1 or $5 or $20. It's astonishing just how hard it is to accomplish when you are clearly giving value, i.e. cash. It also works well as a punishment, e.g. if you failed to do five high fives in two minutes.
- Asking people, men or women, to lightly tap you on the sholder.
- Asking for free stuff at any cafe / deli / grocery store - a free smoothie, cup of coffee, or a donut.