My date wants to tip our restaurant server, my ex; I say no



I was on a date, having dinner at a restaurant and our server was my ex. I wouldn't make eye contact and kept conversation to a minimum. At the end of the meal I didn't want to tip but my date insisted we do. It caused some awkwardness between us after. Who is right in this situation?

Well, it sounds like you’re being petty. Tipping is about the service. So, if your ex gave terrible service that’s not worth “rewarding” then you shouldn’t tip no matter who it was. For as much as an asshole as your ex might’ve been – and it clearly seems like you’re still bitter about the relationship – you look more immature in this scenario.

Not only does it give your ex a reason to feel happy that they’re free of you, it also makes you look bad in front of someone you're trying to impress and start a relationship with.

I have all sorts of issues with tipping: when it’s expected, how much, for which services, etc. But the question customers always ask themselves is, “Was the service worth giving them something extra?” It’s not, “well, I didn’t like her outfit” or “the food that he didn’t cook was cold” – it’s did they do their job to meet your expectations? (There's also the debate if customers should be paying ("rewarding") employees in the first place but that's another column for another day.)

Moreover, if you’re not generally a tipper, then this isn’t an issue. But if you can’t remove the emotion from a business transaction, then that’s on you. I wouldn’t be surprised if your insistence to stick it to your ex – and not in the way you used to – comes back to bite you in the ass – and not the… well, you get it.

This would’ve been a perfect opportunity for you to take the high road and throw around a bit of money, as if to say, “I had a great night with someone new, here’s something to thank you for making it a romantic meal for us.”

Avoiding eye contact also signifies shame so I wonder how badly you screwed up the relationship to feel that small during the meal. Things that make you go hmmmm.