Okay, I actually have three questions:
What’s the most expensive meal you’ve paid at a restaurant that was just for yourself, at a time you were alone (or just paying for yourself)?
What’s the most expensive meal you’ve paid at a restaurant that was for more than one person (like with a significant other or group of friends)?
What’s the most expensive meal you’ve EVER had at a restaurant, period, regardless of who was paying?
Probably around 90 bucks including drinks, several times at both hotel restaurants and Capitol Grille. A couple weeks ago I had a nearly $70 bill at a hotel restaurant without drinks, so if I had imbibed it could have set my record. (Lamb sliders, Bison tips entree with vegetables and potatoes, and a side salad. I was hungry.)
This spring vacation I camped with my family and everyone else took turns cooking a communal dinner. I didn’t because I was a bad cook and we went out for dinner a couple times. We had planned on splitting the bill evenly but I felt bad because I hadn’t cooked and I order a $50 bottle of pinot noir all for myself because they didn’t have it by the glass, so I picked up the entire almost $300 tab.
I don’t think I’ve ever gone over about $15 for myself. One time, though, I was visiting a rich uncle, and he took me out to a seafood place he liked. I had chowder, calamari, and… Oysters, I think? I didn’t see the check, but it was probably in the $50 range.
2, 3. Dinner for two at Le Train Bleu, Paris, about $350 converted to USD.
Maybe $75 for a nice meal at a good sushi place
Maybe $150 for the above for 2
Don’t know since I wasn’t paying, but I’ve been to some work-related dinners with a larger group at pretty nice places that must have run $1000+
Hooooboy, If you count bar bills as meals, probably like $300-$400? buying rounds for the bar and such. Certainly in the $100-$200 range many many too many times for just myself and/or wifey.
I’m no crazy big spender, but sometimes the occasion calls for splashing out.
As a solo female, I’m not in the habit of taking myself out for nice meals alone, especially as I cook well and would rather enjoy such meals at home. But I do go out with friends and pick up my own tab a fair amount. Also a wine aficionado. Best I can recall, I’ve picked up a solo tab for around $120.
The most expensive meal for which I’ve picked up the tab was when I was visiting relatives in Sint Maarten. Took my kind hosts out to dinner along with my mom. I found out how expensive it is to supply food to a tiny island in the middle of nowhere. Dinner for four was nearly $500 converted to USD. No complaints, however. My mom sprang for airfare and I stayed for 2 weeks for nothing except incidentals, so it was a cheap dinner at twice the price.
I can remember two obscenely expensive dinners I didn’t pay for. The first was with my crazy rich uncle (if only he hadn’t procreated!). He took the family to dinner at some hugely expensive restaurant in Saratoga, California, where he lived at the time. He was subtle about the tab, but my dad told me later the meal for 6 was well over a grand.
The second was a rehearsal dinner I attended with my husband for friends who got married on Catalina Island. Both sets of parents were conspicuously wealthy and the parents of the groom sprang for a massive rehearsal dinner at Steve’s Steakhouse, all expenses paid, including drinks. I don’t know how much they spent, but it was a wad. The wedding the next day was held at the Yacht Club and again, open bar along with a very swanky dinner.
The marriage lasted 3 days.
I lost a bet and had to pay about $500 total for the omakase at Sushi of Gari in NY, including 4 beers, for the 2 of us. I paid about the same at the same place when I took my girlfriend there for her birthday.
I don’t usually go to high end restaurants alone, so probably not more than $90 or so alone.
I’m lucky to have a job in which I’m the client for numerous investment firms and insurance companies. I never see the bill but I’ve had more expensive meals courtesy of them.
All of these include drinks which definitely jack up the total bill, depending on what we’re drinking.
Myself: couple of hundred bucks. Easy to do in Tokyo where going out for under $100 was considered cheap (of course, you could get a bowl of noodles at a stand up place for $5 if you wanted to go low end).
With my wife: couple of hundred more bucks
Now with my wife and 3 kids: routinely do $100+
When the company was picking up the tab: It was well over $10,000 for three of us. Literally wining and dining a big client in Hong Kong. He had a massive amount of caviar, and felt like surf and turf (not on the menu) so had a really expensive Kobe beef steak and a whole lobster imported from Maine. None of that was affordable but it was the one bottle of French red wine that really did the damage. Honestly, I’m a beer drinker and would have been happier with a couple of local beers.
For myself $20 tops.
For myself and my wife something over $200
For a group of friends something close to $400
Expensed for business was around $1600
For myself, nothing I can recall.
Took the family out for dinner on beach vacation rather than cook in the rental house with limited pans, condiments etc, family of 15, about $600. AYCE place on the beach, and no, I didn’t pick up the drinks tab.
Another family dinner, celebrating a big birthday, I didn’t see the tab, but it was a high dollar a la carte steak house, and everyone was DRINKING, but I know the tip was over $600. We had an entire crew of servers, and we have a large family.
I was traveling for work and got stuck in Louisville, KY. The only hotel that had rooms was the Brown Hotel downtown, which is absolutely wonderful, and I ate dinner in the hotel restaurant. Due to fatigue or some other mental problem, I wasn’t paying attention to prices, and when the waiter suggested a wine to complement my entree, I simply nodded in agreement.
The next week I had to justify my $140 dinner to my boss!
$240 per person at Alinea.
Business dinner with a bunch of French people, I think there were three bottles of wine consumed before appetizers were done. I didn’t pay, but the tab was over $3000.
1 - Maybe $100-$120. Toronto, business trip on my own. Forget the exact restaurant, but I treated myself to an array of appetizers and cocktails. Beat sitting in the hotel by myself. And yeah, I paid for it - the company I was with was not going to spring for that bill regardless of me being on a business thing.
2 & 3 are the same. Alinea, a special celebration. $1K+change for Mr. Athena and I, and worth every penny.
$120 for two in 1985. That’s (according to the CPI Inflation Calculator) $285 today. Fancy restaurant in DC with the woman who became my wife 16 months later (and to whom I am still married).
Oooh, I’m jealous. One of these days I’m gonna go…
As for the question, haven’t really kept track (and haven’t had a spendy date in a few years…) but I seem to recall throwing down $700 or so at Andre’s in Las Vegas. That was partially due to the cognac selection. Mmmm. I must say, while the food was fine, they offered probably the best (most attentive) service I have ever experienced–being in the mood for that sort of thing that evening. I felt like a queen for a night! 
The restaurant wasn’t very busy that evening, and we were chatted up and pampered by everyone from the bussers to the chef himself.
ETA: Looking at the menu prices now…I’d say the bill was mostly due to the cognac. Ah well. 
Probably $50-$60, and it wasn’t anything special, just a reasonably okay restaurant in NYC. I don’t eat out alone very often at all these days, and the pre-wife “just paying for myself” days were largely also pre-money, so not much opportunity for a big number here.
About $450 after wine and tip at a steakhouse in Boston. It was the night my wife and I got engaged, which wasn’t a particular surprise, and my wife really wanted steak, so we went reasonably all-out.
I’ve seen a couple work dinners in the $2k range for a dozen people, expensed of course. All in NYC, and frankly the food in each case was more “above-average” than “best I’ve ever had”. The most impressive bill was the first company Christmas party I ever went to, at a new office for my company at the time with 14 people, mostly low-mid 20s plus a couple of directors who liked to party. The office was about 4 months old, and small enough that they didn’t bother booking a place, we just went to one of the nicer bars downtown. $1200 for alcohol alone over the course of the evening - in Hartford, CT, so while the drinks weren’t cheap, they weren’t NYC prices either.
Let’s see…
Myself: I think I’ve spent in the $20-25 range a couple of times. I don’t eat out alone often, and when I do, it’s usually takeout or fast food.
Myself and my wife: Probably in the $200-250 range a handful of times, and that’s including wine, cocktails, appetizers, cab ride, etc… Not something we do often, but it’s a lot of fun a time or two per year.
Most expensive? Per-capita, I’d bet it would have been one of the business dinners I was a part of back when I was a consultant. Expensive sushi places in Orange County, lots of expensive sake, beer and wine, etc… ISTR that the bill on one of them was nearly $300/person (most of which was probably expensive booze).
About $25.
About $500, a group of friends at a pretty upscale restaurant (its the absolute most by far, the second highest is about $150)
Several thousand pounds at Restaurant Gordon Ramsey. It was work related, and work paid.
The Melting Pot, I think. Went there for an Engagement party. It was just the enganged couple and me and my (at the time) wife. “Oooh, Melting Pot, we’ve always wanted to go there”. We weren’t so thrilled to get a bill at the end for something like $150 for the two of us (one drink each). We did let them know that since they weren’t treating us (which was fine) they could have given us a heads up that it’s very expensive. We probably would have taken a pass.
Don’t get me wrong, it’s not that we couldn’t swing rent that month, but it was way more expensive than what we’d like to spend on a dinner.
Personally, I can’t see ever going back there again. I’m not big on going to places where I have to cook my food (there’s another restaurant like that), it’s way too expensive and part of the reason it costs so much is that you’re there for like three hours.
By myself, probably about $100 or so at a hotel while on business travel. I love eating by myself while reading a book and people watching.
With my wife, probably $500ish at the Inn at Little Washington.
Most expensive ever was probably some meal with a bunch of people from work, but that was because of the number of people, not the prices per person.