idea @Lipstick_stainsss

Five would always go back in time to when you both first met 1993, and relive that life with you, going through each year with you until you die, and repeating, and that day came, you passed he went back in time to relive that life, but this time, he wanted to change the outcome of your death.

so when he got back to where you both met. It was at the commission on your first day, the handler was walk with you and introducing everyone to you until they walked to him.