Here's a question: do you make guy friends easily?

Because if you have the physical attraction part down, the personality thing is not that different then the way you get to know a guy. Indeed, one of the pieces of advice that worked for me was to treat hot girls like they're guys. Meaning I'd bust their balls, make off-color jokes, talk about guy stuff like sports, etc. Sure, you have to modulate this somewhat, because at the end of the day they're not guys, but you can get 90% of the way there by doing this, especially if they're already hot for you.

So ask yourself this: if you're standing in an aisle in a grocery store in the cereal section and a guy is there, would you ask him "So what are you shopping for today?" Hell no. Maybe you'd shake your head and say something like "Jesus, since when did we get so many fucking choices for a stupid breakfast cereal?! And what the hell does a tiger have to do with sugared corn flakes? I give up. Maybe I should just stick to boiled eggs. How about you? Are you going with the tiger, the honey bee with the big ass, or these weird dwarf elves?"

Bottomline is, you're overthinking this because it's a girl, and you're nervous what she's going to think about what you say, so you play it safe. Don't do that. She'll either enjoy your humor and personality, or she won't. And if she thinks your hot, chances are she'll like it.

Read your post twice, still can't really work out what is going on.

I had to wipe away the tears of mirth when I read "I feel like I’ve accomplished too much with my money, physique, etc" ....yeah, that shit was funny!

What is your issue? It sounds like you have zero game, like none whatsoever, and you feel hard done by because you deserve lots of poon because you are so rich and have such a hot body?

This sounds like rank entitlement.

Maybe those thousands of hours in the gym over 10 years were wasted, if you can't carry a conversation.

I'm gonna tell you a secret:

Women, generally, have no personality at all.

Women who are attracted to you will mold themselves to you like water fills a vase. If they're complaining about your "personality" they're essentially admitting that they're boring as fuck.

Just focus on doing things you enjoy and bitches be damned.

I have the "personality" of a room-temperature radish - I work, I lift, I parent. Occasionally I'll smoke a cigar and enjoy some libations. My current girlfriend for some reason has started hitting the gym consistently, coming to cigar bars with me, and has developed an appreciation for Kentucky bourbon.

I have good news for you, talking about mundane shit is not a bad way to approach women at day. You do have to make it interesting by inserting emotions here and there and try to steer her toward investing in you by baiting her into asking questions.

Taking your example: "What are you shopping for today?" is still too personal and direct. Try instead: "Is that a good brand of cereal?" And talk about those cereals for minutes, how sweet they are, how sweet, or not, you like them, how much fiber they have, does she ever tire of them, milk or no milk. Be fucking autistic about it. Meanwhile try to bait her into asking questions :

"I remember that time at the hotel, they served me very sweet cereal with honey and goat milk... " "Where I used to work they gave us breakfast cereal but they must have bought an overstock because it was always the same brand..." "Where I come from, you could barely find anything with sugar in it, so we had to smuggle some from friends at school..." "At college we had this secret cereal cake recipe we did, we could feed ourselves for weeks on a single batch."

Since you are good looking there's a good chance she will take the bait quite quickly by asking a personal question. Only then can you slowly steer toward asking more personal stuff such as where she's from, where she currently lives, her age, what she usually does around here, her name. Then close by proposing to see her again and taking her contact info as a consequence.

If she doesn't bite quickly, you will have to find something you have in common so you can shoot the shit a bit while keeping on baiting her.

I am struggling at times with this too.

I am incredibly laid back and relaxed, and occasionally have women starting conversations, standing close or strangers being friendly. I go to the gym 2x a week, a huge DIY project in my free time, hiking, over 35s soccer - I am busy, but its hardly that an exciting life and I am amazed at how boring people are.

This might sound arrogant, but every once and a while someone will pay me a compliment, basically show a lot interest and if they have an unexciting life, I can hardly feign interest back. The problem is that's 80% of the population.

If you are craving better connections, I think the best place to find it is through a common hobby, interest, joining a club or even getting involved in some organisation you have a huge interest.

How about joining a mixed sports league something like volleyball? Met a few sports ladies who were solid for a conversation, smart and attractive. I know a gal who plays soccer professionally, her social media is filled with at least 10 simp messages a day - so these women are in high demand, and mostly from men who are at the top of the pile too.

Keeping working on your health, wealth and life - if you are good with money, it will build up, basically keep excelling you'll have women pretty much throwing themselves at you.

Never say mundane things ever. Also, never make a statement that involves a judgement like "I think you are cute." Never make vulgar or sexualized remarks or suggestions.

Try being brutally straightforward. For example, say things like "Do you want to date me?" or "Let's go out... like right now." or "I am going to that bar/restaurant/store over there right now. Do you want to come with me?" or "I have to go right now, but if you give me your number I will call you tonight and ask you out." You can later tone it down and be more indirect and flirty when you get experience, but you should start with very clear and straightforward demands.

Now despite all this, I can’t close for shit. Cause I don’t know what the fuck to say.

Common problem

In my mind I think stupid ass questions like what are you shopping for today etc. sound LAME and look like a feeble and obvious attempt to continue the conversation.

They ARE lame. Don't ask questions, it creates barriers. Make statements about stuff YOU are interested in. Obviously don't talk about your fetish for dungeons and dragons miniatures...... but stuff like "I went to this kick ass live music venue last night" has obvious merit. Live a life that a girl could be vaguely interested in.... that doesn't mean gym bro and cars..... think more like..... social stuff and adventure and trave;.

That’s where I just can’t swallow my pride. It doesn’t feel like the conversation is flowing naturally. It feels like I’m asking the most lame bs to try and keep her engrossed in the conversation. I’d rather not be with her than be lame.

Right.

This has more to with a superiority complex I developed whilst lifting and generally achieving more things in life than “anxiety of what she’ll think” cause it really doesn’t matter what she’ll think. It matters what I’ll think which is that I can’t bring myself to sound like some LAME-O.

Right. So don't.

I feel like I’ve accomplished too much with my money, physique, etc. to have “still put in the work” especially in such a loser way - if that makes sense.

It does but it's the wrong attitude because by saying "I'm a 10,, you have to do the work"..... well, you assume women are capable of doing the work which they are not. She doesn't know you. She may be physically attracted, but she's also weak, scared, shy, worried about her social status, incapable of action and indecisive. If you want to fuck her, you'll have to do the initial leg work of making the conversation work. Typically she'll make this easy if she's attracted.

If it's a more social thing, like a party or something, women will do 10x more work as they get tipsy and get to know you.

On the street..... you're gonna be doing the heavy lifting.

As a result, I don’t really know what to say. Maybe it’s not about what to say and really I need a perspective shift. Either way, hopefully someone can provide insight/guidance.

Don't ask questions, talk in statements. If you want information, make statements...... "I bet you're one of those girls from that posh uptown estate"..... "You look like you're free this evening"..... etc. Make it a game with yourself to never ask questions. You'd be amazed how much smoother things go with girls when you're not doing any asking.

Close with "you seem fun, maybe we should go to that cool bar sometime". This is really easy to cope with if she isnt' super keen, because she never says no. If she DOES say no, you put her in her place..... "I wasn't asking you, I was saying we should go sometime"...... but this almost never happens.

Just have fun with it man.

Through dating apps you can't really tell what the girl is like as some are pretending, others are the real deal (look how they actually act). This is why I prefer talking to girls irl. You get a sense for her personality and can calibrate your humor accordingly - the sensitive types, alright I won't go in bulls blazing. I'll ease her into it. The more liberated daddy issues types, fuck it I'm going in balls on the wall.

Like I mentioned, light hearted jokes and teases work well with every girl besides the super insecure ones, which you don't want to deal with anyway.

Stop thinking about what I have to do to get x girl, but rather, what do I like in the women I get with, that I want to screen for when I meet someone new?

A buyer frame, not a seller. The power is in your hands, they convince you that they are worthy.

Assume you are the prize. Look deeper into your own personal story as to what brought you into the gym. What adversities you overcame to be who you are. That is where you muster your pride. The internal validation.

Do a bunch of LSD, psilocybes, and or salvia.

Youre welcome.