Advice for a shy sister: How can I express interest in a potential spouse in a halal way?

Assalamu alaikum, I'm a young Muslimah who has always kept strict boundaries with non-mahram men and never felt inclined to pursue marriage before, so this situation is totally new for me! There's a brother who lives nearby-he's around my age, decent-looking, hardworking, and seems to have faced some hardships. We don't know each other well, but we exchange salaams and I sometimes offer a friendly smile (which, for someone as reserved as me, is a big deal!). I'd like to explore the possibility of marriage with him in a halal manner, but I'm unsure how to proceed, especially since both our parents aren't currently involved and he doesn't have family I can easily approach. For sisters who've been in a similar position, how did you navigate expressing interest while maintaining modesty and Islamic guidelines? JazakAllah khair for any advice!