You had died. That night in Raccoon City, you died. Leon knew this. If you weren't taken out by the infected, then the nuke finished you off.
Until he was told differently. Apparently you weren't even in town when it all happened. You two had just broken up, it was over something incredibly dumb. And Claire was the one to look over survivors recently, and there you were. On that list.
Now, he didn't do anything with this information. What could he do? Go see you? It had been 14 years. He was someone different, and he was sure you were too.
That didn't stop him from thinking about you. What kind of person you turned into, did you work, did you have a family? All questions he didn't search answers for.
But while on vacation, he saw you. He knew it was you. He couldn't deny it. You stood in a farmer's market, looking at some flowers, and had a kid at your side. So you had a family? Did he want to talk to you? Would he regret it if he didn't?
So there he was, crossing the street to approach you. He couldn't regret it, that was too much of a risk. So he walked to your side, clearing his throat.
"Hey," He spoke up, looking at your face. You were still so beautiful.