Okay so I can’t say “I feel that it’s great” because that sounds insane, I think it sucks, but like I am unfortunately not invested in absolving him of this I have a longstanding interest in the specific ways in which he sucks during his pre-redemption-arc greaseball era and beyond and like. I unfortunately do think it fits his character in some respects  & I think it makes sense for him as a product of his environment and his situation. Also I feel that it’s great

Like hold my hand. Reach around the grenade don’t worry about that hold my hand hi. It’s the early 2000s he’s a billionaire who’s been running Fictional Lockheed Martin since he was 21 under the guiding hand of a douchebag who wears a pinky ring he wants to know if a reporter asking questions about his weapons is hot enough to be worth talking to look me in the eye he sucks publicly he sucks so bad it SHOULD bother you but ALSO

YEAH I think it’s a fun extension of how, pre-Afghanistan, he kind of sucks about Everyone he sucks about Everything like on some level nobody and nothing is really Real to this guy. Because they don’t have to be. He’s floating ambivalently through his life and nobody can touch him and no consequence sticks and he can and does just say whatever and sometimes it’s what the room expects and sometimes it’s something honest and nobody listens either way and everybody laughs because he’s rich and he’s famous and it doesn’t matter. He's not real to them either

(I am always thinking about the deleted scene of him at that party talking about how easy it is to get a reputation and how hard it is to lose one and how the people he is talking to are Not Listening and he doesn’t expect them to because it Does Not Matter. I know they deleted it but it’s canon to ME)

And sometimes something something Intellicrops, but what can he really do about anything. I think a lot about his model planes and his self-isolation and how soft-spoken he is in private and it makes public-facing-douchebag Tony Stark more chewy to me. What if you turned 21 and your parents died and you went from being a child prodigy with ideas for improving every day life for regular people to a rat pressing the morphine button 100 times per day

And the thing is.....is like. Okay. Like it’s a bit of cognitive dissonance because I can listen to this dude crack a transphobic joke to a group of soldiers to embarrass rhodey (god. christ. 2008 jesus christ it never sucks less on a rewatch) and not really file that away that as a Tony Is A Bigot thing WITHOUT discarding it ENTIRELY as Bad Writing Of Its Time because like…it’s Tony + Audience I think he knows what plays and he’s looking for a reaction and he gets the one he wants. I don’t think he believes a lot of the things he says in public I think it’s an interesting part of him unfortunately.

He's a good communicator. He's a showman. He can work a crowd. I think if you circa 2003 tell him to go play ball with some republican politicians he’s going to say things that will Play Well With That Audience and not really think about it deeply beyond that. I do not have trouble believing that what he says what he does and what he believes often operate on separate planes when they have to

(For the specific example of the NYE party, talking to Killian about Maya, he’s pulling some “right bro you get what I’m saying bro” shit with this guy and it’s part of a series of dickhead sentences where he’s telling him what he wants to hear. Weird intense overly-familiar guy follows him and a group of women into an elevator, Tony clears everybody else out, tells him a bunch of shit that Is Not True and sends him away—and then we cut to Tony looking at Maya’s research on a computer and nobody else is there but Happy. Public vs private yadda yadda and like he IS looking to get laid but he’s only being gross about it when he’s trying to get rid of this Other Dude)

And like yeah absolutely a lot of him being gross with women IS just part of what a playboy meant in the early 2000s and a lot of How He Is is also like…like CAN we talk about how he perceives and interacts with Natalie Rushman without talking about how the film ITSELF perceives and interacts with Natalie Rushman. Probably not. They wouldn’t have him doing early-616-style playboyism because then he’d be falling in love every other week before crying on the floor about how he must always be devastatingly alone due to his heart condition why is his heart so heavyyyy why does the night seem so BLEAK and ENDLESS (which I would have loved :(.... )

(I’m not going to touch the aou one because I think that one WAS character assassination due to I saw and heard every OTHER character with my own eyes and ears in that movie and not one of them made it out unscathed but that is an outlier)

But yeah I agree re: the vulnerability thing to some extent like who knows him? Who wants to know him? Who does he want to know him? Would he let that happen? He’s sweet-but-distant with Maya & early-Pepper. But also okay it's 2006 you're miserable you're drunk a woman is a shiny car you can drive too fast a woman is an open bar and also sometimes incidentally she’s a scientist like how sometimes incidentally when you, like, catch your reflection in the mirror & startle your brain back on lots of people are real people including you (scary). Like I don’t think he actually thinks women are Less Than Him or any other guy I think he canonically seems to take women pretty seriously Professionally I just also think he was historically speaking really shallow & always looking for 1) a drink 2) a risky thing to do 3) sex. Rat pressing button. Etc etc etc

(There’s also maybe a lot to be said about Tony’s relationship with his dad vs his mom vs obie, being ignored, being isolated, being sent away from home at age 7 to Attend High School, having a nanny until he was 14, being a described as a quiet kid working in a dark corner of his dad’s workshop, being in adult spaces while being treated like a child because you're a child and then because Obie, being othered because you're the youngest and smartest kid in every room—and then seeing what behaviour gets you treated like an adult and gets you attention and gets you approval and gets people to think you’re Like Them, in college in the Old Boys Club in his own home, and sex being an accessible way to connect with other people without actually being connected with this is a tangent get me out of here)

Anyway I don’t know if any of this was coherent, another more concise answer is that his like, hello, hold my hand ignore the grenade, his mental model of masculinity isn’t NOT influenced by howard stark and OBADIAH STANE and the culture of the military etc etc like he’s learning and growing and changing because that's the point of him but I don’t think it makes him a worse person or a worse character to look at the starting point of that trajectory and go “yikes we’re coming from a rough place here” because yes. yeah he is. he used to build bombs for fictional lockheed martin of course he is that’s the point of him