Obi-Wan remembered their history together. It was why he brought it up. She deserved to know and have it come from him. “So do I,” he says softly, sadly. However, he hadn’t seen any evidence of that when he returned to their galaxy. The Jedi were still gone, Palpatine was still emperor, and he still lived a life in exile.

Following her through the building, he still kept his arm around her, even if he didn’t have to. Wanting that physical contact between them. Which is how it would be until they made it to her apartment and she let them in.