How to Drink Alone and Still Look Stylish

The idea of sipping alcoholic beverages alone often conjures up images of a pitiful figure drowning their sorrows with a bottle of whiskey. Thanks to this stereotype, you may have avoided ordering that solo martini more times than you can count. But, contrary to popular belief, drinking alone doesn’t have to be an act of despair. In fact, it can be a chic and enjoyable experience, whether you're unwinding after a long day or simply savoring a quiet moment with a good book.

The idea of sipping alcoholic beverages alone often conjures up images of a pitiful figure drowning their sorrows with a bottle of whiskey. Thanks to this stereotype, you may have avoided ordering that solo martini more times than you can count. But, contrary to popular belief, drinking alone doesn’t have to be an act of despair. In fact, it can be a chic and enjoyable experience, whether you're unwinding after a long day or simply savoring a quiet moment with a good book.

Here’s how you can drink alone with style and confidence, minimizing any associated social awkwardness:

Start a Conversation with the Bartender or Fellow Patrons

One of the easiest ways to avoid looking forlorn is to engage with the bartender. After all, it’s part of their job to interact with patrons. You can start a conversation about anything—from the process of making a classic cocktail like a Manhattan to the choice of ice cubes used in the drink.

“Why are you shaking it? What’s the purpose of the large ice cube?” Such questions can spark a casual conversation and help you connect with the bartender.

To gain their attention, be generous with your tips and make an effort to remember their name. A person seated at the bar, silently nursing a beer and scanning the room, is likely to attract unwelcome attention.

Bars are social spaces where judgment is minimal. A good bartender will often find a way to introduce you to other patrons, which can lead to interesting connections—be it a potential romantic interest, a new business opportunity, or simply a shared interest.

To increase your chances of meeting people, sit at the bar rather than at a separate table. If initiating a conversation from scratch is daunting, consider visiting bars that host trivia nights or other interactive events. These are not only fun but also help break the ice.

Don’t hesitate to ask the bartender if they’d like to join you for a drink. While many bars have policies against drinking on the job, some bartenders may be willing to enjoy a glass of sherry or amaro if the opportunity arises.

If the bartender is too busy, they might introduce you to a friend or regular customer, providing you with company.

Engage in Ongoing Discussions

There's a fine line between engaging in conversation and prying into someone else's affairs. Recognize this boundary to avoid intruding on someone's personal space.

While at the bar, resist the urge to eavesdrop on conversations. It can appear awkward and intrusive. Instead, try to start a conversation with someone who seems open to it. However, don’t assume that everyone will be eager to chat.

It’s perfectly normal to drink alone at a bar, as long as you’re not visibly mourning over an ex. If you find yourself struggling to keep a conversation going, it’s better to know when to stop. The bartender will likely be busy serving other patrons, and they are skilled at discerning when to shift the conversation back to work.

If the bartender is overwhelmed with customers, it’s not the ideal time to show them the latest funny meme. Similarly, if someone across from you seems uninterested in talking, respect their space.

If alcohol impairs your ability to engage with strangers, consider bringing a friend next time. Bartenders often play multiple roles for patrons—confidant, counselor, or even therapist—so be considerate and avoid unloading too much personal baggage on them.

For instance, if you’re visiting a new bar, there’s no need to dive into the details of your marital troubles with a stranger. While the bartender may sympathize, they’ll likely feel uncomfortable with the level of personal information.

Avoid Losing Yourself in Your Phone

One common mistake when drinking alone at a bar is immediately retreating into your phone. This behavior signals to others that you’re uninterested in socializing, which can deter them from initiating conversation.

Instead, after ordering your drink, lean slightly forward and focus your gaze straight ahead as if deep in thought. Spend a few minutes in this position, and you’ll likely find someone striking up a conversation with you.

Bring a Book

Carrying a book can be a great way to occupy yourself and signal to others that you’re an interesting conversationalist. A good book not only keeps you engaged but also serves as a stylish alternative to staring at your phone. The book’s title can give potential conversation partners an idea of your interests.

Opt for classic literature if you’re ordering a classic drink—like a Rob Roy if you’re enjoying a classic whiskey cocktail.

Be Mindful of Your Space

Avoid spreading your personal belongings around and occupying additional seats, even if the bar is empty. Remember your manners—don’t leave your jacket or bag on a neighboring chair. Use the designated hooks or racks to keep your space tidy and considerate to others.

Choose Your Drink Wisely

Avoid ordering a vodka on the rocks if you want to make a positive impression on the bartender. It can imply that you’re exhausted, tipsy, or ready for your final drink before heading home.

Brightly colored cocktails with umbrellas may send the signal that you’re seeking attention or conversation. On the other hand, a neat whiskey suggests you prefer solitude.

When drinking alone, opt for beverages that take time to enjoy, like wine, whiskey on the rocks, or a dark lager. Ordering a snack is also a good idea.

Visiting a bar during less busy hours and starting with a low-alcohol drink, such as an Americano, can set the tone for a relaxed experience. Progress to something like a highball or a glass of wine or beer as you feel comfortable, but don’t overestimate your capacity.

Keep an eye on your alcohol consumption. Everyone has had their share of overindulgence, but it’s best to avoid it in a public place without familiar faces who can help you get home safely.

Embrace Your Solitude

Order drinks that make the solitude worthwhile—Martini, Manhattan, Belgian beer, fine Scotch, or bourbon. If you’re going to drink alone, savor every moment.

When enjoying a drink alone, relish it as if it’s the last cocktail you’ll ever have. This mindset allows you to fully appreciate your solitary time.

Celebrate the chance to enjoy your own company and indulge in small personal pleasures without judgment. Additionally, being alone at a bar gives you the perfect opportunity to explore new tastes and flavors of cocktails, wines, or beers. There’s no better chance to try something new.

People should not be ashamed of their solitude. In fact, dining, drinking, or watching a movie alone often removes social pressures—there’s no need to entertain others or make an impression, and that’s a wonderful feeling!

Resort to Extreme Measures if Necessary

If other strategies fail, consider bringing an iPad or another tablet—preferably a large one—so that the bartender and other patrons can see what you’re doing. Open your favorite dating app and start scrolling.

Maintain a look of intense concentration, then increase the scrolling speed to a manic pace. When the bartender approaches with a concerned inquiry, respond with a dramatic sigh, “No, there aren’t enough hours in the day to fit it all in.”

Order a Long Island Iced Tea, and as the bartender walks away to prepare it, shout after them, “Make it a double!”