This is what my parents taught me as well. It's not a just a first-date thing, it's a guest thing. If your friend's parents or your roommate's parents or prospective employers take you out for a meal, you order from the middle price range, unless it's very clear from the hosts' cues or from context (for you, Dr. Phil) that it's okay to go more expensive.

Lesson learned: Stop talking just to talk and make yourself clear. :) Manners and moderate are subjective and cultural.

[I have been at gatherings where ordering less expensive or smaller amounts of food was interpreted as the person not having a good time and being ready to leave.]

If this is such an issue for you, find a way to respectfully convey (or politely say) "order whichever entree (singular), 2 drinks, and dessert (singular) that you want." If the "whichever entree" part scares you because some entrees are expensive, take your date to a less expensive restaurant. Look, adults need to stop acting so cautious and scary over things that may be silly in the longrun. You have more exciting things to spend your brain and time on than contemplating and reflecting on a dinner date. Get it said, get it done, and move on to more exciting things.

A smart person who has an issue with what their date is ordering would find a way to respectfully take the lead. Afterall, I would never want to date a man who could not respectfully tell me when to STOP ORDERING if he is the one paying for it. Even a "having to wash the dishes to pay for this" joke can work depending on the context.

Love the Good Will Hunting reference. And I agree with it. Much of what we do while dating is arbitrary, we are just trying to get to know the person better and discern their character, so in fact it doesn't completely matter what we actually do.

Here's a slight twist on the initial question:
Whenever we go out to eat with my inlaws, they always insist on picking up the tab. When I asked my MIL about that once, she said it was important to them that they always pay when taking "the kids" (us) out to eat and that we could make it up to them when they're old and broke. (Note, that ain't gonna happen if I have any say about it).

However, they make it clear when we're ordering that they don't want us to order appetizers or dessert. Don't know the reasoning behind the appetizers but no dessert is because she always has thawed Christmas cookies back at the house so we are supposed to eat them instead (blech).

Now, I know they're well off so it's not a question about them not being able to afford appetizers or dessert. And, hey, sometimes I really want the fried calamari or the artichoke dip. Would it be rude to say, "Well, I want an appetizer so I'll pay for it." or should I just keep my mouth shut?

Perhaps not rude but just unnecessary. It may even hurt their feelings. You can pay for your own calamari or artichoke dip anyday.

Let them have that evening to pay for you with the expectation of no appetizers and no desserts. :)

Yeah, I always figured I could just pay for my own appetizer but wasn't sure if that'd be rude or not. You're right; I can just not get my calamari some other time.

No, this is exactly where you went wrong. "Order whatever you want" - that translates as "hmmm, this dude is trying to be Mr. Big Spender and impress me. Ok baby, it's on. 42 lobsters please!!"

When you take a girl to a restaurant...it's obvious that she'll order whatever she wants. The days of a man choosing the meal with zero input from the woman are long gone. If you feel the need to state the obvious, it will get twisted.

What precipitated you saying "order whatever you want?" Had she asked your opinion on any of the menu items? Had she asked if you'd dined there before?

Her menu selection is one of the many unstated markers that you pay attention to, particuarly on a first date. People will usually, through their actions, show you far more than they will tell you.

Even saying "order whatever you want" should not have been taken as an invite for her to go buckwild on the menu.

She probably didn't go buckwild on the menu. If I knew what she ordered and the total cost, I'd probably so "oh, is that all?"

Speaking of people showing you more than they tell you, someone who says "whatever you want" (not even saying "whatever you want within reason") but doesn't mean "whatever you want," and then doesn't stop you when you need to be stopped, is showing you that they might be a pushover.

I used to do the same thing when I dated, looooooong, loooooong ago and i made sure that our children understood that they should ask their host "what looks good to him/her" if someone was treating them to a meal out. As for those who don't do this, I think the best suggestion was the majority consensus, that a host take a guest to a place well within the host's price range.

Dr. Phil, what great advice to KillarnyRose. Sometimes I know that I don't stop to think that the person treating me is getting pleasure from doing so, and I should just "go with the flow." Thanks for the reminder!

:) This thread is all about going with the flow. Sometimes moderation is the flow and sometimes excess is the flow. :)

lol
Why did you tell her that? I mean, why was that even necessary?

lol

This! FTW! :)

lol

So, if "order whatever you want" isn't an invitation to go buckwild on the menu....what is? If you were out with a girl and you were really into her and really did want her to order the lobster and $65/shot sake (ahem...Morimotos) whether it be to impress her or get her schnockered up, or because you really, truly want her to have WHATEVER SHE WANTS...what would you say?

This was a first date.

If I'm on a first date, nobody's invitation that I "order whatever I want" is going to supercede my own expectation that they are watching, and judging my choices and actions, just like I'm watching theirs.

As others in this thread have said, a sense of propriety, especially on a first date, might have given him a better impression of her in his mind.

How much I agree/disagree with his overall take is an open question (we only know about what he posted) but I can see why her menu action may have put some level of unsureness about her in his mind.

That still doesn't answer my question...

If you *truly* wanted her to order whatever she wanted, without feeling like she's going to be sized up as a gold digger, what would you say other than "order whatever you want"?