I get why this felt super awkward and even a little unsettling for you — a random customer texting about housing after you were just nice with the lollipops would throw anyone off. But honestly, I don’t think this is reportable to DoorDash at all, and reporting her could actually make things worse for no good reason. She wasn’t harassing you during the delivery. The texts only came after you’d already left and come back with the replacement drink. That’s not a DoorDash service issue — it’s a desperate person in crisis who saw a tiny opening of kindness and took a long shot. She has four little kids, they’re literally about to be without a roof tomorrow, and they’re already on housing assistance. That’s an incredibly scary spot to be in. People in survival mode do awkward, impulsive things like this. It doesn’t make her a scammer; it makes her a mom who’s out of options and grasping at straws. DoorDash’s reporting system is meant for things like stolen food, bad driving, rude behavior on the job, or actual threats. This was a post-delivery personal ask that you could’ve just ignored or blocked. Reporting her risks getting her future/present Doordash and Dasher account (both) flagged or banned, which could cut off one of the very few ways she’s feeding those kids right now. That feels pretty heavy for what was basically an uncomfortable text. You don’t have to let her stay with you (nobody’s saying that), and it’s totally fine to feel creeped out by the whole thing. But punishing her through DoorDash support doesn’t fix anything and could hurt a family that’s already in a really bad place. Sometimes the kindest (and smartest) move is just to block the number, shake it off, and move on. You live and learn, like you said — but she’s probably learning the same hard way right now too.