BUILDING SUPERINTENDENT: It is customary to tip your building superintendent $15 for each maintenance request of yours he has ignored throughout the year.
BARBER: It is customary to tip your barber $15 for each person who complimented your haircut and then immediately had sex with you throughout the year.
OFFICE CLEANER: In lieu of money, most office cleaners prefer to receive a handwritten note from the company confirming that its employees will all band together to support them if and when they are faced with a sympathy-inducing hardship, such as a cancer diagnosis or a natural disaster in their home country. The note should also include something about how, in theory, everyone at the company supports raising the minimum wage.
WAITERS: Tips of between 15 and 20 percent for waiters and waitresses are customary throughout the holiday season. Some people claim you should do this all year round, but it is important to keep in mind that it does not say anything about that in the Constitution.
PET GROOMER: Your pet can handle this one.
MAIL CARRIER: I know you have had your heart set on giving your beloved mail carrier a lavish gift worth upwards of $500 ever since you immediately established a close personal relationship with her upon moving into your new apartment, but unfortunately the United States Postal Service does not allow its employees to accept gifts from clients worth more than $20 for reasons no one understands. Try not to let this ruin your holiday season.
POLICE OFFICER: The best way to tip your friendly neighborhood cop is by discreetly slipping him $100 after he has pulled you over for a traffic infraction.
TRASH COLLECTOR: To make the tip more fun, leave a clever little note atop one of your trash cans letting your trash collector know that her tip is hidden inside one of the garbage bags. She will have the time of her life rooting through your refuse and be that much more thrilled once she finally finds the damp, smelly $5 bill!
PAPERBOY: A tip of $100 or more will instantly make your paperboy the highest paid employee at your local newspaper.
ELEVATOR OPERATOR: Elevator operators should receive tips of between $15 and $40 unless they have ever jokingly told you that their line of work “has its ups and downs,” in which case you should immediately report them to the city.
DOORMAN: The best tip you can give your doorman is unsolicited advice on how to invest his money wisely so that he can one day afford to live in a doorman building just like you.
PERSONAL TRAINER: One copy of the classic Bill Murray Christmas movie Scrooged, either on DVD or VHS.
YARD WORKERS: Provide them with at least three detailed proposals for pathways to citizenship that you promise to submit to Congress the moment the political climate around immigration improves.
HOUSEKEEPER: Just give her one moment of genuine human connection, OK? That’s all she wants. That’s all any of us want, really, not just during the holiday season but at any time of year. But think about it: have you ever earnestly looked this person in the eye—this person who has spent six hours at your house every Saturday for the past 11 months—and asked her, “How are you doing?” Not in a trite or meaningless way but in a way that conveys actual curiosity and appreciation for her value as a fellow human being doing her best to make her way through this lonely and isolating world? Or if you’re particularly busy this holiday season, an extra $40 should also work.
ELTON JOHN: You should always tip Elton John at least $175 every December for bringing so much joy to your life through his music.
BILLY JOEL: You can give him, like, $15.