You can just ask the AI to play devil's advocate or constantly keep giving you counter-examples to your theory.
Claude is certainly capable of that. You can tell it how you want it to behave. For example, I told it to be less verbose in its answers and it did so. You can also tell it to be less flattering and agreeable. It's important to coach it on how you want it to behave, not just use its default behavior. "I want you to do x, y, z and not do a, b, c."

WHat in the hell does this long ass run on sentence mean. 

When I first came here some 9 months ago, I did so because I needed help: Years of intense spiritual seeking had robbed me of my zest for life and left me in a state of profound nihilism, derealization and existential angst.
Besides getting accepted into university, I had not much going for me: I was underweight, lethargic and lost in a new country with no friends and social life.
As far as I was concerned, I had completed my spiritual quest and found myself "back in the village," so for the first time in years I had no real goal to pursue.
After a lot of soul searching, I came to the conclusion that I should get serious about the "ordinary" and age appropriate things in life I had neglected so far. Having been extremely competitive my entire life, I knew from experience I could achieve anything, if I really put my mind to it. 
I realized that I would need to find a mentor and that, as much as I admire them, people like Leo, Schmachtenberger and Wilber were not cut out for the job. So after some exploration, I elected German philosopher Friedrich Nietzsche as my guru on time - a choice that would turn out to be way more appropriate, than I could possibly have anticipated.
For those of you unfamiliar with the character of Nietzsche: imagine a mix of enlightened Zen master, ancient Greek sage and sleezy Wall Street hustler. Exactly the kind of guy you want for a job like this.
Nietzsche was a sharp and ruthless critic of truth-seeking, asceticism and compassion and all the adjacent ideals and ideology. The man obviously had his fair share of spiritual experiences and divine insight, which gave him the necessary authority and credibility to talk about these things - and persuade a gentle soul like me to descend to the profane and face human business in all it's ugliness and brutality.
The first thing I took away was to study physiology. I started as a chain-smoking vegan with the libido of a 40 year old woman - I quit smoking, got on an animal based diet, started going to the gym regularly and gained almost 20lbs of mostly lean muscle; I have what feels like unlimited energy nowadays.
The next thing I put my mind to was learning skills. Nietzsche was a big believer in the classical education of liberal arts with a strong emphasis on thinking, writing and speaking. I read over 70 of the greatest books in the western canon, started journalling, went out and talked to 100s of people and started to study sales & marketing.
Finally, I dropped out of college and got myself a hyper-competitive sales job. That might sound like a downgrade to some of you, but having struggled with shyness and social anxiety my entire life, this is absolutely huge for me. I reached out cold to hundreds of businesses and applied myself to be their sales guy - having no prior experience, college degree or anything else to really show for. After a heap of phone calls and me confronting my inner demons and trauma around putting myself out there, I got invited to some in person interviews. I drove 1000km, became sick, got food poisoning and had my wallet stolen - and I fucking nailed that interview.
I'm now moving to one of the biggest cities in Europe to start my new job; I'm jacked and full of zest; I'm profoundly educated in western thought (and I have barely scratched the surface yet); My confidence and charisma has skyrocketed...
What's the catch? There isn't a catch, really. You would think at least my spirituality must have suffered - and while I don't find as much room to be mystical as before, there is still plenty.
I've gotten some profound insight and wisdom from this wild ride, but it really boils down to: what you get out of life is exactly what you put into it.

I'm sharing this, because I see virtually no one acknowledging the deeply philosophical nature of nutrition. This blindspot allowed unconsciously held values of scientists and institutions to bias their research, leading to a deeply skewed definition of "health".
Everything that empowers you is bad: animal products, sugar, etc. Everything that makes you content and satisfied is good: starches, legumes, etc. All the mainstream health and nutrition advice, even the most cutting edge research, is designed in such a way as to make you an obedient little sheep.
For more on the idea of unconsciously held values biasing research and development, check out this brilliant article: https://consilienceproject.org/technology-is-not-values-neutral-ending-the-reign-of-nihilistic-design-2/
What I'm presenting here is an alternative system of nutrition and lifestyle, which of course is just as biased - but towards different values.
This routine is for you, if you value worldly success, excellence and personal greatness. Follow this and you will become an absolute specimen. You will have topmodels fighting over your attention, men crowning you their king. Run away from it all you want, money and power will come your way.
THIS IS JUST A DRAFT SO DONT HESITATE TO EXPERIMENT AND SWITCH THINGS UP
DISCLAIMER: IM NOT AN EXPERT ON NUTRITION AND THIS IS NO MEDICAL ADVICE 
Diet
500g of grass fed ground beef (cooked in grass fed butter, or raw, if you want) + a big spoon of honey 1l of organic orange juice (I recommend greek orange juice, for the best taste) 6 organic free-range eggs (cooked in grass fed butter, or raw, if you want) + shell (balances the acidity of the large amounts of red meat) + Filmjölk/Kefir (+ potatoes, if you want to bulk up) Testosterone Stack
KSM-66 Ashwagandha Root Extract (300-600mg) Tongkat Ali (400-800mg) Fadogia Agrestis (600-1200mg) Boron (3-6mg) Vitamin D3 (5000iu) L-Carnitine, L-Tartrate (2000mg) Magnesium Bisglycinate (1000-1200mg) Zinc Picolinate (25-100mg) Vitamin E - mixed Tocopherols & Tocotrienols (400-800iu) Selenium (200-800mcg) Taurine (3000-5000mg) Testosterone Replacement Therapy, if you need it (I'm 23, so I don't need it and can't speak from experience).
Cognitive Performance Stack
Qualia Mind Nicotine (via Philip Morris's IQOS Ilumina device), for transient peak; NAC (1000mg) to detox carcinogens Coffee!!! Creatine (5g) Additional Supplementation
Athletic Greens AG1 (1 serving) LMNT electrolytes (1 serving) Qualia Synbiotic (for gut-brain support) Habits
9h of high quality sleep - this is a whole can of worms in itself Cold shower early in the morning Sunlight early in the morning HIT weightlifting (1-2 times a week) - check out Mike Mentzer's HIT schedule At least 16h of fasting every day  

It’s basically the path of becoming a master trickster.
You‘ll learn how to be completely fluid in your identity, make up cover stories on a fly (ever tried calling up a big company, asking to speak with their CEO?) and think on your feet — while also cultivating invaluable traits like clear communication, assertiveness, being relatable, work ethic, persistence, fearlessness… which will make a respectable man out of you.
It‘s very psychologically challenging, but also incredibly fun.

Just enter „sales“ in the search bar of some online portals. Look for positions that do not require specific, tangible qualifications. They often just ask for vague qualities like „high motivation“ and „excellent communication skills.“
You should seek out companies that prioritize the sales process over maintaining a polished image. This means avoiding large organizations, start-ups and all „serious“ companies, where your role primarily involves making a few daily calls to existing clients or warm leads, or some bs like contacting prospects on LinkedIn or Email.
It’s absolutely necessary to join a company that encourages cold calling to completely unfamiliar prospects and imposes no restrictions on the number of such calls you can make each day. By engaging with strangers and facing the challenge of generating interest and trust from scratch, you’ll swiftly be forced to get your act together.
It's these positions that I would recommend applying for. Draft a compelling CV and then call up the prospective employers. They love this, because it shows you’re not reluctant to pick up the phone.
The initial phase will be brutal and you will be absolutely clueless, however, even in my first month in a commission-based sales position, I did earn a income of 7,5k (which is not that bad). Being paid solely based on your performance leaves you no choice, but to find a way to make this work.
As you gain experience and hone your skills, it’s entirely possible to make five-figures a month (even six-figures, if you’re really on your a-game). At this point, you can either opt for a more chill work schedule, reducing your working hours while enjoying the financial rewards, or you can commit to mastering the art of sales and further elevate your income potential.

What I recommend:
Owen Cook - Blueprint & Hot Seat At Home (Courses) Leo Gura - How to Get Laid Series (YT Videos) Zan Perrion - The Alabaster Girl (Book) Peter Ralston - Zen Body Being (Book) NLP - Programming your mind to be calm, charismatic, funny. (Books/Courses)

Yes, definitely cut loose and have fun. Be social like you would with any other person. Build rapport through laughing together and relating to each other in conversation.
Women respond most to having a friendly human connection with a man with good conversation, banter, and mild to moderate flirtation.
But as you escalate things physically, the most important thing you can do is to read the subtle sub-communication that’s happening.
It’s the body language and how she responds to your touch that will give you the sense for whether or not to advance a step or take a step back.