Ever wonder what your bartender is thinking when you place an order for that pineapple-based beverage or generic glass of house wine? We picked the brains of 10 bartenders across the country to let us in on what drink you should order to look like you know a thing or two about cocktails. Now does this really matter? Of course not. Here at VinePair, we believe in drinking what you love, whatever that beverage may be. If you love a good dive bar Piña Colada, you just keep doing you. But if you’re curious what to order to look like a boss, the verdict is in.

“A stinger! Cognac, Creme de Menthe served up. When made right, unbeatable. That’s a boss after-dinner drink or after-8 drink.” – Gina Chersevani, Buffalo & Bergen at Union Market

“While I’d normally sing the praises of a Sazerac in this section, I’m going to go in a different direction: the Jasmine. It’s a shaken classic composed of Gin, Campari, lemon juice and Cointreau, and it’s served up. It’s not a common order, so you look like you know something unusual, but nearly every bar should have all of these ingredients, so you’re not forcing your bartender to scramble around to make your ego a point. It’s pink and served up, so if you’re a guy and you order this, you demonstrate that you’re not buying into some stupid idea of “girly” drinks, and though it’s pink, it is in fact a bone dry cocktail, so you’ve got “citrusy, not too sweet” totally covered. This cocktail is a win on every front.” – Lana Gailani, Seamstress & Holiday Cocktail Lounge

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“While I certainly don’t condone this behavior and can smell it a mile away (don’t worry, junior exec, I won’t blow up your spot) you should go with the trends without being too obvious. And most importantly, know where you are! I’d say call for a Boulevardier if it’s a reputable-seeming cocktail bar. If you’re at a Mexican joint, know a tequila that you like and order it on the rocks. If someone comes into my bar and asks for a pina colada, I’ll probably double over.” – Tommy Warren, Bedford & Co.

“I never try to make it apparent [that] I am a bartender or work in the industry. However, I oftentimes get nods of acknowledgement or approval from bartenders when I order a Negroni. I like mine with Averna Amaro instead of Sweet Vermouth. I also like to tell the bartender how I like my martini made to the exact specs in fear they won’t make it properly. Most people have no clue how they actually like their martini prepared so to give the bartender all of that information makes life a lot easier on them. Dry Gin, stirred, straight up with an in and out and lemon twist in a chilled glass.” – Cody Goldstein, NYLO

“Negroni or Tom Collins.” – Joy Richard, Bar Mash

“Any Classic. The best one to order is the Vieux Carré. Cognac, Rye, Benedictine, Vermouth, Bitters… what’s not to like? Only the ones who actually know how to drink, know to pronounce this, much less order it. Good lord I just sounded like a douche!” – Warren Bayani, Chao Chao

“If you can order some obscure but not-too-obscure forgotten classic, three ingredients and the truth type of drink, with minimal fuss and or input into how its made, i.e. none, you will be cool. Order a beer and shot in a busy bar at 3 a.m. and I will know that you know what you’re doing, and tip my proverbial hat to you.” – Jacob Ryan, Four Pillars Brand Ambassador

“Whatever it is that you order, make sure you know the drink, know the ingredients, and know how you like it, but don’t overstate the obvious. If you like a Martini 50/50 (that means equal parts vermouth to gin) you can ask for a gin preference or request a twist over an olive, but you don’t need to ask the bartender to stir it, as that is how the drink should be made. This is, of course, if you are in the right kind of bar to order this. Don’t walk into your neighborhood dive and ask for a cocktail or you will probably get an eyeroll, if you are lucky, and a glass of swill if you aren’t. Don’t try to stump the bartender or order something you once had at another cocktail bar expecting the person to have an unlimited rolodex of every drink ever made by anyone ever. That’s like requesting a cover band to play you a song off your friend’s E.P. Generally, you will look like a boss if you take the guidance of your bartender and you pay attention to what they tell you.”  – Tonia Guffey, Dram Bar

“A Vieux Carré is complex, subtle, and delicious, and I’m always pleased to see guests enjoying them.” – Meghan Kelleher, Distilled

“A Negroni. It’s the go-to for many sophisticated drinkers and any great bartender will make a respectable one.” – John McCarthy, Graydon House