I live and work in one of the most expensive places in the US. My boss had a birthday party that I organized (I’m his EA). We hired a private chef to cater the party. She is a good friend as well. They did an excellent job. When she sent the invoice, she charged $175/hr for her time, $150 for the sous chef (he was paid $100/hr), and $65/hr for each server (they were paid $50/hr). The cost of the food itself was around $3,000. All of those are ok and expected. Total came in at $8k. However, the invoice had a tipping line. I sent it to my boss, since I don’t approve those amounts alone, and in the email asked if he wanted to leave a tip and if I could forward to accountant for payment. He replied that he forwarded it directly.

A few days later, my friend/chef texts me to ask if the tip was coming in a different wire or in cash. I said I wasn’t sure- that I had brought to his attention that there was a tipping option but that I wasn’t the one that forwarded the payment request so I didn’t know what he instructed the accountant. I emailed him, to ask again if he wanted to leave a tip, and he never responded. Which could mean that he missed my email/tip comment a second time, or that he does not want to leave a tip. She has not asked again but I’m sure she will when I see her. Do I need to keep pressing him for a tip? We have hired other private chefs in the past for regular family dinners and they never had a tip line. Just charged for their hourly and the food. Unsure about proper etiquette here, since it feels that everyone involved got paid fair market rates for the service provided, and I generally tip 20-25% anywhere because I know service workers (having been one myself) make under $10/he and rely on tips. Yet that’s not the case here. And frankly I thought it was a little tacky to ask for a tip? Maybe my boss is the tacky one for not leaving one.