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1. J.A.R.V.I.S
J.A.R.V.I.S is Tony’s oldest friend. Maybe it’s a little narcissistic for Tony to say that he loves J.A.R.V.I.S, because Tony did create him and code almost all the quirks that occasionally see Tony making creative threats that will ultimately be unfulfilled. But J.A.R.V.I.S is so much more than just an AI who helps run Tony’s life. He is the only person that can be counted on to keep all of Tony’s secrets, except when he doesn’t, but in every situation where J.A.R.V.I.S has blabbed, in the end Tony has always realised that it was the right thing to do.
2. Virginia ‘Pepper’ Potts
Although their romantic relationship is dead and buried, Tony has somehow maintained an impression of being a functional adult, by remaining friends with Pepper, even though it had felt like his heart had been ripped out when she broke up with him. He doesn’t really like to admit this, not even to himself let alone anybody else, but he is now better friends with Pepper than he ever was before. Whenever Pepper is in town, they gossip about the Stark Industries board members over sushi and one cup of sake, because Tony is really making a serious attempt at being a grown-up. Natasha says in a rather mocking tone that they are ‘proper girlfriends’ now, which always makes Tony think of the Sex and the City show, and he realises that the description is rather apt and he doesn’t even mind.
3. James ‘Rhodey’ Rhodes
Rhodey often questions, aloud in public and often to Tony’s face, why he is friends with Tony Stark. When they think Tony can’t hear them, the high and mighty people at the cocktail parties Tony frequents make snide comments about how Tony really has no friends if his supposed best friend doesn’t even like him that much. However, Rhodey is a lot more like Tony than anyone suspects, in that it’s not the words coming out of their mouths that are important, but their actions. When Tony was held captive in Afghanistan for three months, Rhodey never stopped looking.
4. Happy Hogan
Tony’s relationship with Happy has been fairly uncomplicated, at least from Tony’s end. Happy has been a rock for Tony to lean on for almost two decades now, and Tony can’t imagine a future where Happy isn’t there. Happy has seen him drunk, high, naked, beaten up, and in various other states of disarray too many times to count, but every time his response is the same – a wry grin and an arm around Tony’s waist to drag him out of whatever situation he is in. There was never any judgement from Happy, and Tony will never be able to tell Happy how much he appreciated that.
5. Steve Rogers
If you’d asked Tony a year ago, he would have had some very uncomplimentary words to say about Captain Rogers, and there was no way that the good Captain would ever have been put on a list like this, that is if Tony had ever thought to make this list. Once they’d saved the world and all that jazz, Steve had made his way to the Stark Tower, and J.A.R.V.I.S, the traitor, had led him straight to Tony. Steve had given him the most sincere apology and proved that it wasn’t only the serum that had made him Captain America, but the simple fact that he was a fantastic human being, one who Tony was still not quite sure was real. The apology teamed with sad puppy eyes had crumpled any resistance that Tony might have tried to mount, and Tony had apologised in turn. A month later and Tony considered them friends, a year down the line and they were a lot more than friends. For the first time, Tony isn’t anticipating the end of a relationship, Steve through his words and actions has convinced him that this is real and hopefully forever. Tony still has trouble believing his good fortune some days, but in this moment living in a mansion full of crazy superheroes and Steve lying at his side, he is happy.