Look for a place with more empty stools than occupied ones. The music and surrounding din should be low enough to encourage conversation. A TV above the bar can also be helpful, even if you’re not interested in what’s on. Sports games, commercials and even TV promos are good conversation starters. (“What do you think about Jeremy Piven solving crimes with crowdsourcing?”)
This step may be obvious, but it’s not always easy. Don’t disappear into your phone or wait until you’re two drinks deep to strike up a conversation. Before your first drink, ask the bartender about what’s on tap, or what he or she recommends. Ideally, you want to access their expertise without being an indecisive bore.
When your drink arrives, follow up with a basic question about the bar or neighborhood. “Hey, this is my first time in here. Is the vibe always kind of relaxed like this?” Extroverted people have these kinds of exchanges naturally; as a writer who enjoys long hours of solitude, initiating a conversation with a stranger is anxiety-filled and exhausting.
Fortunately, bartenders are pros at handling this obstacle. “If a person seems genuine, and treats you like a peer of sorts, it’s very easy from there,” one bartender named Dennis told me. Basically, if you provide the critical mass to start the conversation, the guy or gal behind the bar will manage the chain reaction.
Step 3: Order Smartly
You are more likely to get an extra pour from the tap than you are to get a free two-ounce pour of hard liquor. “The cost-ratio is better for the owners, I think,” said a bartender named Amanda, who was clearly uncomfortable with my question as her shift partner handed me a lager on the house. Ordering a glass of wine can also lead to more judicious pours. “I gave [a woman] a whole bottle of wine in two pours,” another bartender named Bryan told me. “She found her husband cheating.”
Some bartenders, of course, prefer to pour a free shot, but you’re not getting a gratis ounce-and-a-half of Fireball because you’ve been ordering Fireball all night—at least I hope not. If you have a preference for hard liquor but still want to angle for a free drink, start with a cocktail, then switch to beer.
Step 4: Be a Regular
If you’re a regular at a bar and NOT getting the occasional free drink for your patronage, then you need a new bar. Being a regular means you can take more liberties: Show up when the bar is busier, engage the bartender a little less, order more whimsically. The more a barkeep can rely on your repeat business, the more freely the free drinks will flow.
And you stand to get more than just buybacks. “I [get] free mispoured beer instead of the bartender dumping it,” a patron named Earl told me. “Pays to be a regular.” Earl understands what all good barflies know: The best-tasting beer in the world is not a Belgian tripel or a small-batch IPA. It’s cold and free.
Shortcut: Either Celebrate or Grieve
Almost every bartender I talked to loved treating people on a special night—a honeymoon, an anniversary, a new job, military officers celebrating their commissioning. On the other side of the coin, as evidenced by Bryan’s heavy pour for a jilted wife, are those suffering through personal disasters and the deaths of loved ones. Recently I texted with a friend who was away from his wife and kids on a business trip. He’d just gotten word that a close family friend had died. “I am now the guy at the bar crying by himself,” he texted. His only company was the bartender and a Rye Manhattan—on the house.
Bartenders, broadly speaking, are social and accommodating people (those who are not are unlikely to stay in the job). They tend to read people well, and while tips may be an incentive, most get professional satisfaction providing their patrons with what they need—from solace to celebration to small talk to support. Or, as one particularly friendly bartender named Sam told me, “I just like to take care of people!” He spread his arms wide to encompass everyone in the bar.
There were five of us.