In a letter to Sharon Steve asks her to thank Tony for slipping money into his account while he is out on his trip across the county and mentions their poker nights. Captain America V. 1 #700
set in the distant future where Steve is one of the handful of first generation Avengers alive. He succumbs to his loneliness and buys a companion OS who fashions itself into someone very familiar.
in other words a Stevetony Her AU (that ive been working on since AI Tony was anounced lmao just pretend that sophisticated AIs arent a thing in 616 OR they’ve recently just been opened to the market and back then its just tony who has the capabilites to have AI)