At a recent work party in New York City, Brady Dunayer, a 28-year-old real estate banking analyst, bolted to the bar to order a drink. He was startled by what he received: His whiskey-based cocktail was served in a stemmed glass and garnished with a flower.

The presentation, he thought, was “a little out of the blue” for a whiskey drink. So for his next round, he ordered the same cocktail but told the bartender, “Hold the flower, give me a rocks glass.”

That same night, Daniel Kaye, a 26-year-old working in finance, wasn’t thrilled with the fruity cocktail he’d ordered at Commerce Inn while out with his buddies. He said the highball glass, complete with a striped straw, made him feel a little feminine. “I didn’t love it,” he said, adding, “It was a masculine venue, a lot of whiskey being served.”

There are many reasons a bartender will serve a cocktail in a particular kind of glass, dilution and aeration among them. “The 30-something finance bro doesn’t care about that,” said Kyle Kuhl, the head bartender at Rocco’s Sports & Recreation in NoHo.

While efforts to challenge the gender binary are evident in how we talk, dress for work and wear makeup, a visit to the cocktail bar might transport you back to the 1950s. Bartenders say that many men appear as committed as ever to drinking out of “manly” glasses and avoiding glassware they deem too feminine.

“It’s an industry joke that we tend to stereotype people based on their glassware preferences,” said Kaslyn Bos, 30, a bartender at Donna in the West Village. At Donna, the drinks are colorful, sometimes heavily garnished with fruit and cocktail umbrellas and often served in “shapely glasses,” she said.

Ms. Bos has fielded requests — only from men — to transfer a cocktail from one glass to another. She noted that a manly glass, to those asking, is always a rocks glass.

At Rocco’s, Mr. Kuhl’s solution is a color-coded glassware guide on the cocktail menu. A blue dot means the cocktail will come in a rocks glass; a green dot signifies a coupe glass; and a brown dot denotes a novelty glass (one is shaped like a football).

Mr. Kuhl has noticed more glassware imagery popping up on menus since the pandemic. “More and more cocktail bars are leaning into it a little bit to mitigate the surprise” for the customer, he said.

Glassware choices are important — for instance, Mr. Kuhl serves the Serena Chilliams, a take on a French 75, in a coupe glass so the drink is neither diluted with ice nor warmed up by the customer’s hand. His menu provides fair warning.

The system requires some degree of glassware knowledge, but it does the trick. “A younger guy said to me, ‘I was going to get the Cherry Bonds, but then I looked up what a Nick and Nora glass was,’” Mr. Kuhl said. (The Nick and Nora looks like a shorter version of a stemmed wineglass — potentially non-manly.)

In his 2019 book, “Alchemy: The Surprising Power of Ideas That Don’t Make Sense,” the advertising executive Rory Sutherland wrote, “A few years ago, we discovered that men were reluctant to order a cocktail in a bar — in part because they had no foreknowledge of the glass in which it would be served.” The fix, Mr. Sutherland found, “was to put illustrations or pictures of the drinks on the menu.”

In a video with more than 2.4 million views on TikTok, Max Klymenko, who also works in advertising, presented that revelation in “Alchemy” to a new audience. The conversation in the comments mostly confirmed the book’s findings: One response, from a bartender, read, “I’ve seen men freak out about a straw.”

“It’s just a matter of what you see in TV and movies,” said Mr. Klymenko, who added, “I vividly remember Harvey Specter on ‘Suits’ always drinking from a short glass. To me, that seemed like something I should emulate.”

At Shinji’s in the Flatiron district, the menu includes illustrations for every house cocktail, which are all served in specialty glassware. At the Up & Up in Greenwich Village, the cocktail menu has both illustrations and a key showing rocks, highball and stemmed glasses. Ali Martin, the cocktail director, said the intention was only to communicate the drink’s strength or dilution, but for people who want to drink exclusively from rocks glasses, it does save a step.

“As a society, we’re working toward dismantling gender roles and gender dynamics,” said Haley Traub, the general manager at Attaboy, on the Lower East Side. “Why is this the one little thing that we’re still holding on to?”

Ms. Traub said she is disheartened by the lingering trope of the man’s glass, but she doesn’t see it changing anytime soon. “As much as you want to shake the person by the shoulders and say, ‘Stop gendering glassware,’” she said, “it does help to take the opportunity to explain and educate, and hopefully change their viewpoint.”

Jake Webster, a 24-year-old working in finance, used to succumb to the desire for a stemless glass. When he first started going to bars, he would order a beer or a whiskey on the rocks. Eventually, he grew tired of ordering drinks he didn’t like.

Despite stares from “some dudes in bars, usually the Chads in the room,” he said, his go-to drink is now a Cosmopolitan, served straight up in a V-shaped glass.

“It’s 2023,” he said. “Who cares anymore?”

Follow New York Times Cooking on Instagram, Facebook, YouTube, TikTok and Pinterest. Get regular updates from New York Times Cooking, with recipe suggestions, cooking tips and shopping advice.