Wow. Good question. I'd probably go ahead and order it because I'm worth it. (I really wanted to use that smiley.) But really, I probably would still order it if it was what I really wanted, but I would offer to pay for it or at least buy dessert or something.
I wouldn't order something *just because* it was most expensive. I usually don't like expensive stuff anyway.
I'm an eater- fairly tiny person but it goes somewhere DBF and I went out to brunch this morning with another couple and a different table (who we knew, not strangers) picked up our bill for us. We didn't know until we were all finished with the meal. Turns out DBF and I had decided to go all out each ordered a ton of food and shared. But then again, we were starving.
When I was dating different guys (before DBF), I always took my cue from them AND the place- If you go to the diner and the most expensive thing on the menu is $10, I say go for it if that's what you want. If the most expensive thing on the menu is $45 i suggest picking something else.
I think it also depends on who is paying- is this guy a 21 year old college student without a job or a 35 year old lawyer well on his way to partner driving a Jaguar?
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