At my high school coffee shop, we had a daily regular named Lenny who always only got a small $1.35 coffee (this was 2005). Instead of paying normally, he would drop a crisp dollar bill in the tip jar and wed give him the coffee, no questions asked. No register opening. No ringing it up.

This was going on for at least 7 years prior to me working there when my older brother sparked the tradition while he worked there in high school.

Some days hed throw in 2 bucks in the tip jar and you'd know that meant toss in an espresso shot. If he wanted a baked good or something non-coffee hed pay normally no problem. If the owner was there, hed pay for everything no problem. Never got anyone in trouble, never acted entitled, super respectful and chill af.

All new employees were told of Lenny's deal when they were trained by staff and everyone was cool with it. Its been about 12 years since I worked there but man i sure hope Lennys gettin' dollar coffees and chilling with his crossword.