You are not stupid. You just want to help somebody who you feel deserved it. Whether you saw him 3 times or 333 , it's irrelevant. Don't overthink it , just send what you feel like. Your good karma will follow .
In beginning of Covid, upon learning boy I met only once but was very impressed with, got stuck in his native Cambodia and took very low job , just to stay afloat, with help of forum friend I sent him some money. Boy barely remembered me if at all and yet, 2 years later when we met by chance in soi 4 he recognized me then, thanking me several times. Rest i.e. subsequent multiple offs is just a history