The rumors about Tony and Henry weren't entirely untrue. After a while, being wasted and screwing supermodels became routine, so it was only natural to slip up sometimes--that there arms would brush even in whatever huge bed they'd tumble into, that their legs would twine in a hot tub while being ridden by swimsuit models, that wasn't a big deal.
Henry never knew how much Tony remembered in the morning, if he had the same flashbulb memories of searing kisses and callused hands (though Henry's hands were much smoother than Tony's, taking him immediately out of any fantasies he created as soon as he'd try to touch himself). He had to admit part of why he pushed for Tony to join AA was a selfish, tiny little spark of hope that maybe he could be as intimate with a sober Tony as he was with the perpetually drunk one he had known.
And Tony Stark's sponsor had to spend quite a bit of time with him. Henry jumped way up in Tony's speed dial and soon enough it almost felt as though they were dating. Henry had a few weeks of thinking something might happen, of holding Tony through crying jags and whispering in his ear over the phone in the early hours of the morning. It was intimate and, he hoped, it showed Tony that he cared, that he could be trusted. But making any romantic overtures would have been taking advantage of a friend, so he bided his time.
Right up until he noticed the looks being exchanged between Tony and Steve Rogers, how close the two stood or how often they were together. And he realized that he'd waited too long. And he continued being there for Tony, all the time suppressing whatever regrets he felt.
It was with not a small amount of shame that he found a silver lining in Captain America turning against Tony during the Civil War. It was his chance. And then when Rogers was assassinated he could no longer think in terms of being Tony, everything was about keeping Tony sane. He jumped at the offer to lead the Order, knowing it meant working closely with Tony, and he tried to find new alternatives to how they used to hang out, new hobbies that might get Tony out of the suit and away from all of his stress.
Inevitably, after a night spent flying above Los Angeles, they fell together into Tony's too-neat bed (leading Henry to wonder if his friend ever slept) and got everything they'd hinted at to each other all those years before. It was thrilling, scary, and repeated every change Henry got.
Now he got to add a whole new reason to hate himself to the mental list he kept: the hope that, when someone or thing eventually brought Captain America back from the dead, Henry would be the reason Tony broke his heart.