How to fuck up the first date

Dating and dining red flags with Right On Franklin's Olivia Weiss

I get antsy in between my quarterly visit to New York, missing out on the more fun restaurant scene of the two coastal cities in which I spend most of my time. Thankfully, Olivia Weiss helps satisfy my fix from afar. Olivia runs right on Franklin, a great resource for everything from hyper-specific New York food recs to thoughtful provocations on modern dining. I first found Olivia’s writing when she reviewed Bridges before I could, which annoyed me as a deeply competitive person.

Olivia and I also share a passion for telling our friends where to go on dinner dates. I hold a very firm “no food on the first date” rule. (You need to be able to dip after the first drink, and I also don’t want to ruin a place I like on an internet stranger). But there can be real magic in a second-date dining experience. I’ve done everything from tacos to tasting menus early on in seeing someone. These meals reveal a lot about the person you’re getting to know. Someone can charm you with their approach to ordering for the table or give you the ick by explaining natural wine in too much detail. And that’s what we’re here to dive into today — dinner date red flags. It’s the season of love and that means the season of bad decisions.

Olivia: Picture this: You walk into a first date ready for a few martinis and a good time. Your date, a perfect stranger, is wearing flip flops—dogs out. You let it slide, but that’s a 10 point deduction. You eat a snack and sling back a few drinks. The bill comes, he pays, and promptly says (in front of the waiter), “we’ll figure it out later.” Noted.

I don’t actually know what that means, but alludes to an IOU in the form of anything from an incoming Venmo request to another round you have no choice but to pay for.

I’ve been on a large handful of first dates in New York City and have a pretty okay grasp on the dating landscape, hence the many iterations of date night recommendations. That said, the dating faux pas I’ve witnessed, experienced, heard about, even committed, are fraught with debate and also kind of hilarious.

As you read the list below, keep in mind that Austin — a man of good taste — and myself, a lady with really strong opinions, very well might be the problem. What follows is just a peek into mildly insufferable levels of judgment. We’ve given you the spots, and now you’ve got some notes on etiquette, too. This is a meeting of the minds I don’t think you knew you needed. You’re welcome.

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Dinner date red flags

A: Not even looking at the dessert menu.

O: 100%. I can’t live a lifetime with someone that doesn’t care about sweets. You have to at least look. Also, please don’t leave it to me to decide if we are going to pass on the final course.

O: Earnestly ordering an espresso martini.

A: I probably wouldn’t do this on a first date — I mostly stick to old fashioneds and negronis — but fwiw I earnestly ordered an espresso martini as my first drink at dinner last week and I stand by it.

A: Asking the waiter to choose between two wildly different dishes as your entree.

O: I can respect some mild decision-making anxiety, but this is an embarrassing interaction to witness. The only thing worse is a date that modifies a dish. Order it as it was intended!! Grow up!!

O: Complaining about your waiter/bartender.

A: There’s a flirty version of this that can work. Like, sharing a few tasteful jokes about how overeager a server is. Fine. But, yeah, FOH criticism isn’t hot first date material.

A: I don’t think I can handle a just-water drinker. Sparkling, soda water bitters, tea, coffee, whatever — if you only drink tap throughout a whole dinner date I’m a little shook.

O: This kind of person has a mental stamina I will never understand.

O: Complaining about the food — that’s third date behavior at least.

A: Disagree! I’m attracted to good, opinionated taste. It’s lame to spend an entire meal talking about the food. But if a dish is bad let’s chat about it a bit before going back to flirting.

O: The correct answer is, “I pick the place, so the food is never bad.”

A: Mispronouncing an ingredient or wine region. Either get it right or don’t try. (Sorry).

O: This is your meanest take but I don’t disagree. I appreciate an eager attempt and I think asking questions is a green flag, especially if you are out of your depth. It is tough to watch someone swing and miss, though. I do get concerned when I am asked what an ingredient is. The obviously obscure ones — totally fine, let’s be confused together and guess. If you don’t know what fennel is, I will not be calling you.

O: Showing up late.

A: I’m habitually 15 minutes early to everything, and basically always give a 15-minute grace period beyond the agreed upon time. That 30-minute window is a good opening to play Backgammon on my phone or flirt with other people at the restaurant. More than 15 minutes late is a red flag, though, for sure.

A: Ordering the caviar supplement.

O: Or just ordering the most expensive thing on the menu … you’re either peacocking or being an asshole.

O: Ordering something super heavy or rich. If you’re ordering alfredo or, like, a milkshake I will be scared but maybe also impressed.

A: This feels to me like fling vs. relationship behavior. I’d have a fun fling with an unhinged orderer.

A: Having a good appetizer and then immediately ordering a second serving

O: Who the hell does this lol

O: Uses Dorsia or pays for reservations. Weird behavior.

A: Having inherent connections is hot and paying for them is not. Agreed.

A: Booking an outdoor table. Spending more than $75 a person to eat outside is a fucking sucker move, and not good date behavior no matter the time of year.

O: I’m lukewarm on this. I think a first date at the tables on Canal outside Cervo’s is fun and sexy. A summer sunset is romantic. In almost any other circumstance, outdoor tables are not the move and seem like a last resort. Work for that primetime spot.

O: Shows up in shorts or flip flops.

A: One time I went on a third date with a girl much hotter and more interesting than me. She wore fuck you sweatpants that were slumming it even for LA. I was slightly into it as a kind of power move, but, yeah, overall, not a fan. It’s hot to dress up for a good date.

A: Spending literally any time looking at your phone.

O: Unless you are showing me a picture of your dog. Agree.

O: Mentions Carbone as a metric for their “good taste.”

A: Date or not, I end up asking everyone I go out with for their spots at some point during the evening. The answers matter, but how they answer matters even more. Are they looking for a scene? Infatuation approved clout? Purely good food? Convenience? You learn a lot very quickly.

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Burning questions

Who picks the spot?

A: I do. Usually a spot at least a little closer to yours than mine, but generally convenient for both. Probably like 15% nicer than you were expecting but still accessible. I’ll pick it with confidence but leave the door open for you to veto.

O: I do not remember the last time a guy confidently picked a first date spot. I think I do it every time. Generally, I am happy to, with the guarantee it will be a perfect vibe and convenient for me. If we are on date three and I am still picking the spot… no sir.

Who pays and does the girl need to pretend to reach for her wallet?

O: The story I opened with did happen last summer, and was one of the very first times I didn’t reach for my wallet during a first date. He was clearly not happy that he had to pick up the bill, which was a signal I should have taken more seriously as a clue for what was to come. Now, I am about 70/30, not reaching for my wallet versus trying to split. On the first date, it is sweet to be taken out. AND, I’m a cheap date and won’t pull out my wallet to pay for three beers. First couple of dates, guy should pay, and do so with confidence. As time goes on, especially if substantial dates are a frequent occurrence, splitting the bill or rotating who covers is perfectly respectable. This is my most tradwife take please don’t hate me!!!

A: I have a longstanding belief that men have done enough horrible nonsense that we should spend the first few dates proving we have our shit together enough to pay for whatever the planned excursion is, small budget or big. I think it’s particularly attractive when someone keeps the conversation going and doesn’t pretend to reach when the bill comes. Even in a long-term relationship, I pay for nearly every dinner and then finances even out in other contexts. There’s just some romance in it.

Do you need to disclose preferences/dietary restrictions beforehand?

A: Our texts about this question are potentially cancellable lol. But, look, if something is gonna kill you then yes, go ahead and flag it. If you merely have aversion, I think the adult think to do is shut the fuck up.

O: If you are picking the place, I sure hope you’ve picked somewhere you can eat the food. If I pick and you are allergic to everything they serve, please tell me. We are on the same page on the aversion front. And I quote, keep it to yourself. Respectfully.

What’s the appropriate amount of drinks to drink on a first date? At what number do we start getting concerned?

O: At dinner, two drinks or half a bottle. If drinking is the main event, though, three is the golden number. On my best first date we went for a fourth round of beers because we didn’t want the date to end — but that is beer-specific. Four to five negronis, martinis, or spirit-forward cocktails is a different story. Frankly, I will get nervous and it’s not sexy to make your date uncomfortable/worry about you.

A: I’m big on sharing a bottle. Otherwise, I think at least two drinks at dinner is solid. You could do a third over dessert or, even better, at a second location, where there are no limits. If someone hits drink No. 5 the first time we have dinner together I don’t know if I’m concerned or intrigued, but I’m certainly clocking it.