Ask The Salty Waitress: Is It Wrong To Expect My Mega-Rich Friend To Pay For Dinner?

Dear Ms. Salty,

One of my friends happens to be a wealthy executive of a multi-national corporation. The guy is loaded—upper-six figures rich. When I first got to know him and we dined out, he would almost always pick up the tab. It would become this implicit thing — he would happily pay for the meal, $200 meant nothing to him, and everyone went home happy.

However, the last 4-5 times we dined out, he would be the one initiating the dinners, and it would often be at some high-priced place. And each time, he would nonchalantly say, "Let's split this?"

Look, there's nothing wrong with this; I make a comfortable-enough living to pay for dinner. I still enjoy dining out with him, every time. But yet, there's a tiny voice in the back of my mind thinking: "You cheap bastard." Should I feel guilty for even thinking like that?

Riding Coattails in Calgary

Dear Coattails,

Everyone should be lucky enough to have one rich friend—not too many, because then you become an insulated country club ratbag, but just one who sometimes lets you drive their Ferrari, swim in their heated pool, or eat out on their dime.

Asking to split the check among two adult friends isn't wrong or impolite, even if the voice in your head says that he could wipe his ass with $100 and not notice. He's not being rude by asking to split the bill, but the question is whether you're wrong to wish he'd pick up the check again every once in a while.

Now that the Champagne train's left the station, it's time to think through why your friend's behavior could have changed. Maybe something got shaken up in his personal finances? I don't know what's going on with mutual funds or petroleum futures, but is there a chance that he's doing a bit of belt-tightening because of changes to his own financials? Best not to pry, but there could always be something going on that you don't know about.

On that topic, does he think something's changed with you? New job, new house, new million-dollar trust fund? Maybe he assumes that because you started ironing your shirts, you've really hit it big.

I understand your reaction, even if it etiquette says there's nothing wrong with what he's doing. Maybe splitting the check is a sort of litmus test he uses once he's gotten to know someone and wants to make sure they're not just using him as a meal ticket. Maybe he's afraid the string of free meals will feel awkward for you. Or maybe he thinks "Hey, I've picked up the tab the last four dinners. When is Coattails in Calgary going to spring for the check?" (Look, I don't know how rich people think, I'm just spitballing here.)

If you're finding the dinners a bit rich for your blood, you could always suggest a less-pricey alternative. When it's your turn to offer the invitation, skip the French spot with the wine vault in favor of something more casual. You didn't mention how your friend orders when you go out—do you spend about the same amount on each of your meals, or is he a can-I-get-a-side-of-caviar type? If it's the latter, then splitting the check could be slightly unfair.

Oh and if he starts picking up the tab again, feel free to invite your old friend Salty along to thank her for the swell advice.

Got a question about dining out etiquette? Or are you a server/bartender with a horror story the world needs to hear? Email us: salty@thetakeout.com.