I've only seen it once so far, but I feel like Bucky gave him a nod right before he went back. Sort of an unspoken way of him saying "Go get her, live your life."
Also, I believe Steve was still Captain America when he went back. He just got off the plane this time, and was active for however many years, just married to Peggy. I also believe that Peggy still died at the same age in the timeline, which is why Steve was alone on the bench.


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