On Ordering the Expensive Thing
There is a specific flinch that happens when nobody is watching you spend money on yourself. It is worth examining.
Notice what happens when the menu comes and you are by yourself.
The eye goes to the right-hand column first. The reasoning starts: it's only me, I don't need the whole thing, I could just have the one course and eat properly at home. You order down. You almost always order down.
Now notice what happens when you're taking someone out. Suddenly the tasting menu is reasonable. Get the good bottle. Of course we're having dessert.
Same money. Same stomach. Different audience.
What that's actually saying
It's saying the expenditure needs to be witnessed to be justified — that generosity is a performance requiring a second party, and that spending on yourself with nobody watching is somehow closer to waste.
Which is a strange belief to hold, and most people holding it have never once said it out loud, because it doesn't survive being said out loud.
The correction, in practice
Order what you would order for a guest you liked.
Not the most expensive thing on the menu — that's just the same flinch running in reverse, spending to prove something. Order the thing you actually want. The one you keep glancing back at. Frequently it is the second-most-expensive thing, and frequently it is the best dish in the building.
Get the glass of the good wine rather than the bottle of the fine one. Solo dining has an economic advantage nobody mentions: your budget goes roughly three times as far. The dinner that would be extravagant for two is merely a nice Thursday for one.
The receipt
Keep it for a while. Not for accounting — for evidence. It is a small, dated, itemized document proving you spent money on your own evening and the world did not end.
After the third or fourth one, you stop needing them.
More from The Practice
The Table for One Is Not a Consolation Prize
Somewhere along the way we decided that eating alone in public was something that happened to you. It isn't. It's something you do — deliberately, and better than most people do it with company.
The Phone Is the Third Wheel
You did not bring yourself out to dinner to watch someone else's evening. On the difference between being alone and being unaccompanied.