'Where's the red flag?': Awkward date dinner ruined by woman's faux pas after her date orders expensive food

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Remy Millisky • Writer and Editor
Mar 10, 2023 3:00 PM EST

This super awkward dating faux pas is keeping one woman awake at night. While on her third date with a guy, the OP suddenly found herself feeling uncomfortable with what her date was ordering to eat. 

As u/Upper_Somewhere5005 told r/AmItheA**hole, she's been talking with this guy for about two months, and for their third date, he told her he wanted to treat her to the meal. This took the OP by surprise, because her date had apparently been pretty frugal on their previous dates. She was then even more startled when their meal began — her date ordered several appetizers and "one of the most expensive items on the menu, plus sides." 

At this point, the OP freaked out a little, and asked the waitress if they could have separate checks. She was convinced that this guy giving her major red flags. However, commenters told her that she was probably being a bit of an a**hole to this dude who just wanted to pay for a nice dinner for her. This OP played it safe this time, but her date probably won't want to offer to treat her anymore. 

Next, this guy was so proud about the petty revenge he got on some "entitled models," only to have the internet roast him for being presumptuous. 

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  • 01
    Nature - 'AITA for asking to split the check?'
    via Matthieu Huang
  • 02
    Font - r/AmItheA hole Posted by u/Upper_Somewhere 5005 5 hours ago AITA for asking to split the check? This happened tonight and has kept me awake.
    via u/Upper_Somewhere5005
  • 03
    Font - I had a third date with a guy that I've been chatting with for 2 months. First time we're going out to dinner (his suggestion -- picked the place and wanted to "treat me"). It's not a cheap place by any stretch.
    via u/Upper_Somewhere5005
  • 04
    Font - We get there, are making small talk and looking at the menu. I am hungry and decide on an entree. Ask him what he's ordering and he's "undecided". Waitress comes back to our table with our drinks and we start to order. I order my entree, and then he proceeds to order a few appetizers and one of the most expensive items on the menu plus sides. I'm a bit wide eyed at this, the waitress kinda gives him some side eye but writes it down. Maybe I've been on reddit too much but a red flag warnin
    via u/Upper_Somewhere5005
  • 05
    Font - Waitress says "sure -- that's not a problem" and goes to put our order in. Guy is sitting across from me red faced, says "why separate checks? didn't you hear what I said? I wanted to treat you tonight." I realize I really don't have a good reason for it without outright S ing on his character so I say "I appreciate that you wanted to do that for me -- I feel more comfortable paying for my entree." He kind of mumbled a fine, excused himself from the table for a bit, came back and the rest
    via u/Upper_Somewhere5005
  • 06
    Font - My friend group laughed at me and couldn't believe I did that. Notable comment was "Dude was going to buy you a nice dinner and you basically sit on him at the table." I still view his ordering habits as a red flag but since not a single person in that friend chat said I wasn't an as hole...aita for asking to split the check?
    via u/Upper_Somewhere5005
  • 07
    Font - Updating to answer from frequently asked things: - He had stated previous dates that he was being extremely frugal due to some major financial goals he had. Our first two dates were very inexpensive. The dinner was a surprise based on his comments previously. - Its not how much he ordered or what specifically he ordered, but the cost alone -- it was well over $200 and it made me uncomfortable.
    via u/Upper_Somewhere5005
  • 08
    Font - - I didn't know the restaurant, and didn't have time to look it up ahead of time so I wasn't aware of the cost until I sat down. Paranoia came from a TedTalk I had watched, plus some major anxiety around dining/money that I have.
    via u/Upper_Somewhere5005
  • 09
    Font - I accept that I was an a hole for how I did this (I should have brought it up when I first realized the prices on the menu at minimum and not when the waitress was there especially if it made me uncomfortable) and will be sending him an apology once it's more into the morning.
    via u/Upper_Somewhere5005
  • 10
    Font - Far-Juggernaut8880 - 4 hr. ago Colo-rectal Surgeon [37] YTA- he offered to pay for dinner and you accepted the offer but in front of the server changed your mind without warning. That was very rude and dismissive. Not sure why his ordering was red flags to you. But certainly not enough to be so judgmental and rude.
    via u/Far-Juggernaut8880
  • 11
    Organism - underonegoth11 . 4 hr. ago I treated my partner to several extravagant meals.in the beginning...glad they didn't walk away because I was trying to spoil them
    via u/underonegoth11
  • 12
    Font - bluebloodsydney. 2 hr. ago. edited 2 hr. ago I'm not a fan of gender norms, but if OP was a guy it'd be easier to understand her paranoia/concern that her date had ulterior motives and would dump her with the bill. She wasn't tactful, obviously, but I can see why the situation made her nervous.
    via u/bluebloodsydney
  • 13
    Font - kidunfolded 2 hr. ago I don't know why she has such an issue if he's literally paying. If I'm paying, I'm ordering whatever I want LOL. So what if he gets an expensive entrée? He's picking up the check! It would be one thing if he ordered all that when they were splitting/sharing the check, but that's not the case.
    via u/kidunfolded
  • 14
    Font - Ladyughsalot1 - 2 hr. ago I think it's weird to order excessive appetizers without once asking your date, who you apparently want to treat, if they have any interest in those appetizers. Maybe his intent was positive. His execution was off.
    via u/Ladyughsalot1
  • 15
    Facial expression - mollybrains 1 hr. ago She said the server was giving him side eye - as if it isn't the server's job to upsell
    via u/mollybrains
  • 16
    Font - honey-smile. 4 hr. ago · edited 3 hr. ago Colo-rectal Surgeon [38] INFO: where's the red flag?? Edit: I'll give you a NAH (leaning towards Y TA), but this was your own paranoia more than any real "red flag". Definitely sounds like a too-much-internet-for-you moment.
    via u/honey-smile
  • 17
    Font - DetailHour4884 - 2 hr. ago Not OP (or a woman for that matter) but I could see a red flag as being some undiscussed expectations that come with the "treat" of such a meal. Dude had already mentioned his need for frugality w/ her previously and their other dates didn't approach that kind of expense, so I could see how OP might get paranoid about the change in situation without really understanding why she felt that way.
    via u/DetailHour4884
  • 18
    Font - ravencrowe 49 min. ago Yeah I don't get it. It was his OWN food that he chose to spend a lot of money on, if he insisted she get the most expensive thing on the menu I could see being worried he'd expect her to "owe" him but why is him getting himself an expensive meal a problem? Just weird to me.
    via u/ravencrowe
  • 19
    Font - Future MissMD. 3 hr. ago I'm on the fence, leaning towards YTA... Men (+woman, and all beings) are allowed to have savings goals and still spend. I've literally had guys order more food and more expensive foods while on dates and have never batted an eyelid. Seems like you have some insecurities or anxiety (which is fine, we all do) when it comes to money and dating.
    via u/FutureMissMD
  • 20
    Font - MushroomItchy7180 - 4 hr. ago A hole Enthusiast [6] YTA for assuming anything because of his totally normal order. Maybe he WANTED the surf and turf with a baked potato and creamed spinach (or whatever)? No idea why you'd go on a date with someone you're afraid would stick you with the check, you should have either declined, suggested a less expensive place or made your wish of going dutch up front. You did sh all over him at the table.
    via u/MushroomItchy7180
  • 21
    Font - pendingsweet 3 hr. ago I don't think it was about being stuck with the check, I think it was about not knowing what his expectations were about how she could "repay" the "treat".
    via u/pendingsweet
  • 22
    Font - Thatsaclevername 50 min. ago Yeah I agree with this one here. The paranoia in this thread is insane Imao. Also something that feels left out is that it's only their third date 2 MONTHS into seeing each other. I mean jesus imagine thinking someones into you for that long, go on another date, and they have this weird little freakout about being stuck with the check. Did he talk to you for 2 months to get one free dinner out of it? I feel bad for the guy. OP must be beautiful with great conv
    via u/Thatsaclevername
  • 23
    Font - DoraTheUrban Explorer 4 hr. ago . Colo-rectal Surgeon [36] NAH It's fine you wanted to pay your own way, but he wanted to treat you and you didn't let him. I doubt the waitress gave him any side eye, if it's an upscale place she's used to people ordering food. The restaurant wouldn't exist if people always came in and ordered minimally. Maybe in the future if you're not comfortable going to expensive places with newer dates why don't you start your first few dates getting coffee/lunch not
    via u/DoraTheUrbanExplorer
  • 24
    Font - Upper_Somewhere5005 OP 4 hr. ago That's what threw me tho -- our first two dates had been frugal by his own suggestion (he has financial goals that he wants to make -- it's a big deal to him). We're talking coffee on our first date, a hike and burritos on our second date. I was shocked by the prices when we got to the restaurant -- I'm not familiar with it, and didn't get a chance to look up the menu before we went otherwise I would have suggested somewhere else.
    via u/Upper_Somewhere5005
  • 25
    Font - deltagardevoir. 4 hr. ago A hole Enthusiast [9] I'm gonna have to say a soft YTA. I get that some people get scammed, and it sucks, but if you go your whole life with the first instinct to avoid scams you're never going to be able to trust anyone new ever. Unfortunately this is the consequence, now a guy who most likely did want to treat you (especially after 3 dates) now thinks that you don't want that, and probably was able to tell why. If he's saving up for a house, that's fine to be w
    via u/deltagardevoir
  • 26
    Font - Upper_Somewhere5005 OP 3 hr. ago I accept my fate with this. I appreciate your insight, and while I hope we can have at least another chat where we can clear the air and part as friends I'll consider that a lesson learned.
    via u/Upper_Somewhere5005

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