How Pete Davidson Got Engaged To Ariana Grande

To all the depressed, anxious, funny lookin’ dudes out there who complain about their dating issues, Pete Davidson is a balding, insecure, anxious, funny-looking 24-year old dude who has Kroehne’s Disease and oh yeah his Dad died on 9/11.

And swiftly after breaking up with Larry David’s daughter Cazzie, just a few weeks later, is now engaged to one of the biggest pop-stars in the world, Ariana Grande.

Pete is the kind of guy who, despite all of the absolute shit things in his life, seems to just stumble into greatness really fast.

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Test: Do you compare to Robert Downey Jr's charm? Choose the answer you agree with most 🤯


How did he get on an MTV show? His agent knew someone. Then he met Amy Schuymer and he got a small part on Trainwreck. He met Bill Hader who tried getting him on SNL with an audition. He met Lorne and Lorne was like, “You aren’t really good for SNL but I’ll let you know what happens.” Then a month later Lorne calls him and is like, “Okay you’re gonna be on the show, see you at work.”

He did standup for his SNL audition. Nobody does standup for their SNL auditions!

So what does all this have to do charm?

I think there’s a lot you can learn from ol’ Petey when it comes to charm. Before I get into the deep stuff, right on the surface, Pete is the type of guy most people would want to be friends with. He’s just cool.

His style’s unique, he’s hilarious, and he’s honest as fuck. And to get further into his honesty, Pete is like… crazy honest. Seemingly to a fault. But that’s the exact trait that I am sure Ariana and his past girlfriends found so attractive about him. This is what separates charming men like Pete from loser fuckboys, players, pickup artists, etc. Charming dudes are super real and vulnerable people. You look straight into their eyes and there is not one fishy thing about them. It’s like this with Pete, too. You can tell there’s not an ounce of facade. And that’s why I think gals dig him. Confident women hate meeting a guy and sensing some sort of hidden ulterior motive. Don’t hide anything.

But at the same time, Pete has every shitty thing in the book that could happen to a guy in his twenties. Basically, with what he deals with on a daily basis, he shouldn’t be getting the success he has or date the successful, positive women he has.

Most people I know with crippling anxiety and extremely low self-image are not able to do what he does.

Being completely comfortably open about your weaknesses is a huge secret to being crazy attractive to women. Most guys think that being confident is about hiding every little negative thing about you and only presenting your strengths and power. This is so, so wrong. You literally want to do the opposite.

It’s a fine balance, this vulnerability thing. What does comfortably open about your weaknesses mean? It doesn’t mean that you talk about your problems and then minimize them, acting as though they don’t bother you. That’s still hiding. But on the other end, it also doesn’t mean that you are constantly venting to everyone you meet, and are visibly affected and emotional at every moment. That’s, well, pitiful.

Then what does it look like? To be completely comfortably open means that you can talk about your issues or shortcomings as though you’re talking about the weather, and then move on to something else. You can even joke about it a bit (but not too much or it’ll be obvious that it’s an act).

Like let me show you something about me to give you an example: I used to be really insecure about my nose as a kid. When I hit 8th grade, every one of my Anglo-Saxon white-ass friends had these cool names like Jake Volf and PJ Turzo and Daffin Reed. Then I hit puberty and Anthony Recenello with the big Italian nose and the name nobody could ever pronounce, not even once, stuck out like a sore thumb. I hated it, I cried to my mommy so hard that one day she printed out a picture of all the attractive celebrities with big noses to make me feel better.

Tell me, would you ever admit to Ariana Grande that you actually replaced the teeth you have in your mouth? Or that you’re balding before you’re 21 and getting treated for it with Propecia? Or that you were diagnosed with Borderline Personality Disorder? Or that you think you’re, quote, “Fucking ugly” and that you also have a disease that makes you shit literally thirty times a day? Does that sound like something Ariana Grande would get fucking turned-on by?

The truth of it is yes. She would and she does. Because confident, attractive women don’t want pretty boy perfectionists. There’s no character about them. They’re all “charisma” and facade and have zero charm. Charm is about embracing who you are, scars and all.

You know what I think? I think that Pete just has such a whirlwind of shit constantly happening in his life, that holding it in would be too much. He’s mentioned his bouts with suicidal thoughts before. I think that he realized he can actually function as a human being when all of his issues are out in the open. He’s released the demons! There’s no more hiding for him. And he can kind of relax in that way, knowing there’s a tornado of shit flying around him instead of erupting inside of him. Actually, that must be how he feels. Pete’s life is a tornado, but he himself is the eye of the storm in the center that has learned to be calm and functional.

I honestly think that the biggest part of people’s problems isn’t the problems themselves, but constantly trying to act as though the problems bubbling inside aren’t there. It’s therapeutic to be at peace with your issues. It will feel like a relief once you air it all out.

He met Cazzie David on the set of SNL back when Larry was doing the Bernie Sanders impersonation. Ariana was also a guest on SNL, but I don’t think that’s where they made a connection. It was a year later in early 2018 when Ariana attended an SNL after-party and both parties had ended (or were in the process of ending) their former relationships. Knowing Pete’s stumble into success, my guess is they just felt comfortable talking to each other being the two youngest people in the room. Pete doesn’t look the type to yuck it up with the other cast members, and maybe they connected on hip-hop music or tattoos or some shit.

As much as Pete mentions how much his classmates bullied him in high school, he seems to embody the type of guy that’d be super popular and attractive in my hometown as a teen. Tattoos, tall and skinny, a real hip-hop fanatic, expert joint-roller, laid-back, and pointedly funny. Kind of like Bill Burr on acid.

And I want to go back to the way Pete interacts with people. He has this thing that I think is more important than any other quality or skill. When he’s interacting with someone, he’s what I like to call “engaged”. What I mean by that is there is nothing more important at that very moment than just taking in the person in front of him. He has a calm Presence when listening. Everyone thinks that to be a good communicator you have to have exciting things to say, and all that shit. It’s completely false. All you need is to be Present with the person. Nothing should be going on up in your head. There is no “move”. There is no master plan. There’s no trick. There’s nothing he’s trying to gain. I think that’s Amy Schuymer saw in him, I think that’s what Bill Hader saw, I think that’s what Lorne Michaels saw, I think that’s what Cazzie David saw, and I think that’s was Ariana saw.

Because while the rest of the world, especially the entertainment world, is working on constantly feeding the beast of validation inside of themselves, Pete has dealt with enough shit in his life to know to keep it at arms’ length. Because that’s when you can see people and things clearly in front of you for who and what they are instead of what you want from them. So to everyone else, it looks like you’re doing some sort of magic trick. “Why does it look like he’s not trying to impress everyone? Why does it look like he’s not a slave to the addiction of climbing the social ladder or becoming more famous or more rich?” I think it’s because of the tragedy of his father passing at an early age he’s realized on a deep level that those things are fleeting and mean little compared to the simple enjoyment of having the opportunity to live. It looks like magic to people and in turn is compelling and admirable especially to the famous people who are around scum-fuck blood-sucking star fuckers most of the time and crave someone that can purely just look at the “you” behind the “you.”