But I just had another headcanon revolving around the post CA:CW headcanons I have.
What if Tony didn’t throw the engagement ring back at Steve but simply kept it in a safe place because he’s still not ready to move on? It resides in the very same dark red velvet box that Steve had used to keep the ring and he keeps it in one of the drawers in
their his dresser.
One day, he decides that he wants to send it back to Steve (he thought about giving rid of it but he couldn’t bring himself to do it) and he’s in the workshop, got his envelope ready and everything. But the more he looks at the box, knowing what’s inside, it becomes all too difficult again because he still hasn’t let go of his still very there feelings for Steve.
So, he leaves it in the workshop and forgets about it for the next week as he buries himself into his work while also taking on mentoring Peter.
Peter discovers the engagement box during working with Tony in the lab and curiously, he picks it up and opens it.
“Wow, Mr. Stark, are you planning on proposing to someone?”
Tony looks over, eyebrows furrowed in confusion before catching sight as a sudden rush of emotions go through him. He remains quiet long enough for Peter to get worried and go to him before gently placing a hand on his shoulder.
“Mr. Stark…are you okay?”
He snaps out of it soon enough and tries to fake a smile with a nod of his head.
“I’m good, kid.” Tony replies before giving a shrug. “And no proposing here, it was just a-”
“Will you marry me, Tony?”
Bright blue eyes and a hopeful, kind smile.
His smile turns bitter.
“Just something that was left by someone who used to be a very good friend of mine. The engagement didn’t work out…unfortunately.”