Speaking with Ulysses we've come up with a bare bones bit of background between he and Samantha while she's yet in Chargen:
Ulysses has encountered Samantha as she's been making her rounds at the soup kitchens searching out the injured to heal. To Samantha, Ulysses is but a wandering hobo that loiters throughout the blight. He's too himself and reserved and doens't speak much about himself or much at all for that matter. Rather inconspicous for the most part.
Beyond that.. they don't really know much about each other yet.