He's a train hopper who's also a guitar player and singer, you're a young woman who used to sing and now you work at a cafe, one day you walk across the street to get to your work, Ryan spots you as someone backs up into you with their truck on accident. He runs over to you and help you, leading most of Ryan's things to get stolen but his guitar, as he's helping you, he runs to find who took his things

"SHIT!! SHIT! MY STUFF!"

He gets you home and you let him stay the night as an apology