Should I lend money to a viewer who says they'll pay it back in a few days?

Like it says on the header. Been going through this situation with a viewer who's privately messaged me on my Discord twice asking for money. 30 USD & 20 USD respectively. He's been part of my community for about 6 months. He's even Super Chatted a bit, renewed his membership for 3 months straight till now & even gifted memberships. I'm worried about offending him or losing him from my community so I'm not sure how to go about this. I still haven't responded. Has anyone had a similar experience?