New York-based dating influencer and content creator Anna Kai went through a phase in her 20s when she only ordered Old Fashioneds, or the occasional Negroni, on first dates.

“I hate those things,” she says. “I’m not a spirit-forward drinker. But I wanted to be taken seriously, almost by the drink I ordered. So I just stomached it.”

Kai prefers those sugary, so-called “girly” drinks — the sweeter and more opaque, the better. But knowing full well the perceptions she was up against as an “NYU girl who likes sugar in a glass with alcohol,” she sought to present a cooler Anna: the sort of girly girl who prefers what some might traditionally call “men’s drinks,” like extra dry Martinis and Old Fashioneds. Restaurant industry HR director Ashley Kappa has another way to describe why she similarly ordered mezcal Negronis to impress on first dates, which were almost always with chefs: “It made me look not basic.” (It helped that she actually finds mezcal Negronis tasty.)

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Then again, we’re not really talking about alcohol in either scenario, even if we technically are, Kai says. “We’re talking about psychological manipulation in dating when you’re trying to present a certain version of yourself, which stems from insecurity.”

We’ve all trotted out an augmented version of ourselves on dates or when we’re otherwise trying to impress, at work events and the like. If said scene happens to take place in a bar — as much of life does in our culture — what better way to tantalize, to appear cultured and interesting than with a flex cocktail order?

The flex cocktail can take up many guises, depending on who and where you are and who you’re with. Some keep their flex drink classic — a Martini or Manhattan — impressing through ratios, spirit swaps, or inversions. Some order cocktails that explicitly defy stereotypes or vibe-check their companions; some hope their cocktail prowess will spark curiosity or a conversation, or maybe just get them laid. Several people I polled copped to ordering certain cocktails mostly because they sound sexy when uttered aloud: Vesper. Last Word. Bijou. Boulevardier.

“Boulevardier?” Kai says. “That’s French, I assume? Anything French sounds like an orgasm.”

If we’re paying close enough attention, the flex cocktail order can expose our own insecurities and warn us of potential red-flag behavior; it can even help us figure out what we really want in our glass, out of ourselves, and sitting across from us — for the foreseeable future, at least.

Confidence Is Everything

Bartender Rachel Miller hasn’t been on a date in a while, but her go-to has long been the Black Manhattan, a variation with bittersweet Averna amaro standing in for the sweet vermouth. “Drinks like the Black Manhattan are classic, and most decently stocked bars can make them, though it usually gets a pause from the bartender,” she says. “It has a little bit of ‘amaro-is-cool’ points, and comes in a sexy coupe. Win win.”

Miller, who tends bar at Chicago’s creative Japanese hotspot Kumiko and co-owns the bar supply store Kit, has seen plenty of first dates from behind the stick. The Black Manhattan in many ways sums up her key to a good flex order: confidence.

“Part of it is confidence that the bar can make it,” Miller says. “I don’t think it’s a flex drink if you’re like, ‘Hi, I’d like a Blue Owl,’ and the bar is like, ‘We don’t know what that is.’” (In fact, this scenario could more rightly be deemed anti-flex.)

The other half of the confidence piece is owning what we like, which might also be the hardest thing to do when we’re meeting someone for the first time. Making matters worse for our poor psyches, we only get one first-impression drink. Kristin Olszewski, founder and CEO of Nomadica Wine, is still haunted by the memory of a 30-something man ordering a vodka Sprite on their date. “All the attraction left my body,” she says.

On the one hand, dude likes what he likes, and his vodka Sprite affinity would’ve come out sooner or later. But could he have stood to make a bit more effort, say with a prickly, citrusy French 75 instead? Kai has found the postering flex to be a slippery slope. “Wanting to impress through cocktail prowess is a facade, and that stuff wears down very quickly,” she says.

Knowledge Access and the Dreaded Money Flex

Regardless, cocktail prowess, even in small doses, can be intriguing — and occasionally helps cull the herd. For bartenders, the flex comes in the nuance and the intensely flavored: ordering a mezcal Campari dealer’s choice, or asking specifically for sweet, herbaceous cuishe mezcal. It might take the guise of “opting out of the game because you’re above it,” Miller says, like a bartender who goes out and orders a rum and Coke. Most tantalizing of all, though, is to call up the ultimate flex drink: the Very Specific Martini order. There’s dry, and then there’s dry in the sense of “give me a quarter-ounce of vermouth, and make up the rest with gin.”

Restaurant general manager Jill Zankowski will order a two-to-one Martini less as a flex than to vibe-check her date on vermouth. “Typically I learn that the person I’m on a date with doesn’t drink well,” she laments. “I’ve been in restaurants many years and trying desperately to date outside the industry, but when normies don’t have good taste in drinks or food, it’s a red flag for me.”

For us normies, on the other hand, cocktail prowess is whatever levels us up to a higher-knowledge realm. Finance and accounting consultant Joe Borgese rarely strays from the classics: Martini, Old Fashioned, or highball, depending on the time of day, preferring to flex through the specificity of spirit and proportions. Depending on your (and your companion’s) knowledge base, however, cocktail prowess can look like an Old Fashioned or ordering an Aviation as an excuse to spark a conversation about crème de violette.

For illustrator Jasjyot Singh Hans, mezcal alone suffices to intrigue him, especially when it crops up somewhere less expected, like in a Negroni. “I remember when I first heard someone get [a mezcal Negroni] I was, like, confused, intrigued, mildly turned on,” he says. “I think whenever people order mezcal instead of tequila they do an invisible hair flip. It’s a weird pretentious flex where they imply they’re so familiar with mezcal as a spirit that this is their go-to cocktail.” Then again, he adds with a laugh, “it worked.”

Knowledge flexing is not to be confused with money flexing via sceney, pricey spirits orders — a major red flag to Miller. “If there’s a guy who’s like, I need Johnny Walker Blue Label, that feels like flexing a display of money,” she says. “There’s a way to do it, saying, ‘I genuinely enjoy this and have enthusiasm for it. Do you want to try?’ Or there’s the dismissive version, like ‘I only drink Macallan 18.’”

Augmented Reality or Fantasy?

Contemporary art gallery curator and art historian Laura Augusta would sooner order the fanciest bourbon on the menu than a flex cocktail on a date, especially since moving to diminutive Rincon, N.M. This is partly a hedge since she lives in a rural place where the cocktails can be hit or miss, plus it gives her an enjoyable, quick-draining out if things go south. But she orders bourbon more to explicitly stamp out any gender-based stereotypes.

“On dates, since I date men, I think there’s often a misconception that I’ll get something girlier,” she says. “I realize this whole scenario is loaded with gender stereotypes (much like dating).”

Indeed, one of the toughest parts of putting ourselves out there is gauging how we think we’re being perceived alongside our own reactions to the person across the table, and judging the lengths we’ll go to impress while keeping our own perceptions in check — all while attempting to remain present and — oh, right — enjoy ourselves in this minefield of obvious and cleverly hidden agendas.

Because isn’t this all supposed to be fun in the end? And whether we’re ordering a Wet Martini or a Bacardi and Diet, shouldn’t we do so because we like it first and foremost, which in the right company is the biggest turn-on there is?

“Actual enjoyment is really important; never lose sight of that,” Miller says. “ Find that thing that is interesting to you. And try to push it a little bit further.”

Toward the end of her dating career, Kai embraced the so-called basic when she finally decided to own her love of girly drinks. “I started to give no f*cks near the end of my 20s,” she says.

She got married last year, in fact, some time after a successful first date in which her now-husband ordered a Penicillin and she ordered a decidedly non-flexy Pinot Grigio “and about 10,000 glasses of water” because she was getting over a cold. In other words, exactly what she wanted.

“Now I literally ask the bartender or server, ‘Is this drink girly?’ That is the term I use, and they always know exactly what I mean. I’m just that kind of drinker, and I love that about myself now.”