@boringwriter 21 May 2021 more from that month

If they are feeling down and you said “DON'T GIVE UP. KEEP IT UP” on their problems, I'm sure that they will only receive it as a form of toxic positivity. Hence, instead of asking that, ask instead, “Are you having a hard time? You can share it with us”. By the means of that, you might give him a solution on his problem and responding do not give up will not even pay his bills.