1.) Howard and Maria Stark
The first time Tony lost someone was on December 16, 1991.
He could still remember the silent house and how loud the ring of the telephone had sounded in comparison.
Could still remember how cold his feet had been as he stood there on the cold floor, not able to move even by an inch.
Remembered how an unknown voice had talked in a soft tone, one usually reserved for small children who were scared and about to cry.
But Tony hadn't been a child anymore.
Hadn't been a kid since his 14th birthday were Howard had gotten home drunk at the end of the day, not even acknowledging his son besides a slap to the face for staring too long.
Anthony Stark couldn't have afforded to be a child, couldn't have afforded to be helpless and dependent.
So in true Stark fashion he had done what was necessary, he had become and adult in order to survive.
So, no.
Tony hadn't been a child on December the 16th in 1991.
But then why had he started crying like one?
Where had the ugly, round tears come from?
If Tony Stark had been an adult since the age of 14 then why had he felt so lost at loosing his parents?
Why had he cried for hours, alone in a house too big for one, or even three people?
Tony hadn't found out.
(He didnt want to admit to himself that maybe he couldn't hate his parents (Howard...) as much as he wanted to.)
Maybe he never would.
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2.) Ho Yinsen
The second time Tony had lost someone close to him, it had been in a dark cave in Afghanistan.
Unlike the cold he had felt while being notified of his parents passing, all he remembered was suffocating warmth.
The electronic pulse in his chest, the fire of his suit, the blazing heat of the sun above and at last the hot pain shooting trough his entire body, traveling throughout his entire nervous system, making his vision blurry.
He also remembered hot rage, blinding anger and the sweet taste of revenge of his tounge
Many had died at his hand that day.
Looking back, it had been foolish and even if it hadn't been unjust it hadn't been heroic either.
Looking back, Tony Stark would choose to do things differently.
But back then, May 2009, in the glowing heat of the desert, bruised and traumatized, it had felt like every life he took had been one step closer to bringing Yinsen back to life.
It had been the foolish hope of a foolish man who had been desperate to repay his debt to a man that had saved his life.
Too bad not even Tony Stark's brilliant mind could bring back the dead.
Or could it?
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3.) Jarvis
The third time Tony Stark lost someone important to him it had been his fault.
Had he been more careful, more open with the rest of the team...if he had been better.
If Anthony Stark had been a better man in 2015 then J.A.R.V.I.S. might still be alive.
If he hadn't been so, so.. egotistical then his oldest son would still be alive, developing, berating him for his behavior.
J.A.R.V.I.S. would still be there for him, invisible but ever present.
Maybe Cap had been right all along.
Maybe if Tony Stark had been more like his father then maybe everything would still be alright.
Maybe then the walls of the tower wouldn't feel as cold as they do, maybe he then he would still be able to feel J.A.R.V.I.S.'s warmth around him.
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4.) Himself
The forth time Tony lost someone it was himself.
At first, he had thought that it had been an old friend he had lost, that the hero he grew up being jealous about, now walking away from him, was the one he had lost.
But lying there on the ground, cold sweeping in trough the cracks of his destroyed suit, mighty shield still embedded in his chest, he had realized.
Realized that he had never had that kind of friend, that Steve Rogers wasn't who he had lost.
No.
Shutting his eyes, head falling back down to the hard ground, cold biting at his skin, Tony had realized that it was himself he had lost.
Had realized that he was truly and utterly, LOST.
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5.) Peter Parker
The fifth time Tony Stark had lost someone he was directly there to see them disappear.
There was no call, no dying man behind him, no death behind closed doors.
There only was a boy in his arms, begging- BEGGING him to stay, telling him how afraid he was, telling him that he doesn't want to go-
The fifth time Tony had lost someone it was the second time he had lost a son.
Peter Parker had died in his arms, had fallen apart to dust before his very eyes.
And with him Tony's world fell apart as well.
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+1
Over the course of his life Tony Stark had lost many people.
He had lost his family, his friends, his faith.
And he had mourned, mourned for the things, the laughs, the souls he had lost.
Over the course of his life Tony Stark had learned that loss was permanent.
He had learned that bringing back the dead was pretty much impossible.
Tony Stark was always one to push the realm of possibility.
So it was no wonder that even death would eventually fall to its knees in front of Tony Stark.
Peter Parker stood before him
again, 5 years after his death, smiling as bright as the sun and death bowed deeper.