Food & Drink

When Bartenders and Regulars Become More Than Just Drinking Buddies

Mark Yocca / Supercall

I will never forget how the EMTs that frequented the first coffee shop I ever worked in took their medium hot chocolate and coffee in large cups to avoid spillage in the ambulance; that the Second Avenue subway contractor, who hadn't touched booze in eight years, preferred lemon in his water but no straw; that Janet in East Hampton liked to finish her first glass of North Fork Chardonnay before ordering the roast chicken, all the while glued to a romance novel. There is an intimacy in reading your regulars—those folks who come in week after week or even day after day. You come to know instinctively who is having what sort of day, what liquid will salve which wound or set the mood just right.

I suppose it's addicting, this knowledge that someone is coming back just for you, that you hold the power to make their day by setting down their usual before they even ask. But it’s even more of an opiate when you start to feel the same way about them.

One night after I got off work, I reclined in the corner of the bar with a few coworkers and a bottle of wine. As we bantered, I noticed a handsome stranger nervously alight on a barstool and order a beer. "Bar four is hot," I whispered to my friend (also my manager), who promptly snagged the bartender and made him send Bar 4 a shot on me. I raised my wine glass, prepared to "cheers" him from across the bar as soon as he looked up to thank me. I waited, my glass growing heavy. I watched the shot, untouched. He sipped his beer. He went to the bathroom. The shot began to sweat, or maybe that was me—we were both feeling overtly ignored.

Then, as if by divine fate, an unruly birthday party gathered around him, demanding drinks and jostling him out of his seat. The guy, his beer and my shot relocated to a table directly behind my stool. I looked at my friend, the two of us utterly confused—why in the ever loving hell was he not saying thank you or, at the very least, taking the damn shot? Behind the bar, the bartender was equally amazed. He grabbed a dollar off the bar and yelled, "Hey, bro, you forgot your change!" As the stranger approached to take "his" dollar, my friend spun around and said "Hey, this is Jena. She works here, and now you have to say thank you for that shot!" He stared, wide-eyed, and stuttered hello and that he lived upstairs. We began to chat and then, without word or warning, he disappeared out the door.

Friday rolled around again, and I was just about to sit down and pour myself some wine when in he walked—Bar 4. He sat down, ordered a beer, and this time, he struck up a conversation.
For the better part of a year, I had a fake date every Friday night with the regular from upstairs. The last half hour of my shift, he would arrive and try to score his favorite seat, right at the end of the bar where he knew I would sit to eat my dinner and have a glass of wine. If I sat at a table, he would join me. We laughed, we flirted, he occasionally brushed my arm or found an excuse to lean in closer. But, in an entire year of fake dinner dates, the man never once asked me out. Not once.

The role of bartender/friend/flirt/performer can feel like a balancing act at times. In the act of listening and building a relationship with a regular, it's all too easy to feel human first and forget all about the structure and rules that come with the exchange of goods and services. Yes, there are plenty of professionals who don't you-know-what where they eat, but for every one of those there is also the perfect alignment of energies that leads to something else. Is it laziness or hope that urges us to see where the night takes us in the place we spend a majority of our time and, in theory, make a living? If Bar 4 had asked me out, what would've happened then?

"My first bar gig in New York, I had a regular from Spain,” my friend Elijah said, sipping his vermouth-heavy Manhattan. "She was always drawing in her notebook at the bar, but she would never show me what she was rabidly sketching. One night, my friend glanced over her shoulder and realized she was drawing me! He came up to me and said, 'Dude, ask her out!'" Elijah laughed. “She said yes to a beer. She was only in New York for the summer finishing her degree. One night, I took her to DUMBO and we went on the carousel. I took her hand and leaned over and kissed her. It was crazy hot. We were both kind of drunk and started fooling around on the subway on the way back—there was no one else on the train and so we took it up to the next level. I won't lie, I'm a bit of an exhibitionist." Images of Tom Cruise in Risky Business began flashing in my brain as he continued. "It got to the point where we'd have sex everywhere. She'd wear a lot of skirts..." He trailed off, a gleam in his eye. "I was closing the bar one night and, as we were about to leave, she turned off the lights and said 'close the gate' before leading me back to the bar. My manager texted me the next day and said, 'Yo, stick to the back left corner next time! Our cameras work.' She moved at the end of the summer; the break up sex on my roof was incredible."

Elijah's story was fresh in my mind when I went into work the next day and found myself across the bar from one very hungover friend. I slid her an iced Irish Coffee and asked, "Hey, got any 'and then I did the bartender' stories?"

"Boy do I," Elizabeth laughed. "I mean, I definitely had sex in the manager's office during the World Series. I was a patron and he was working and we had a quickie during his shift." I resisted the urge to bust out a home run joke.

"This was a guy that had also lifted me up on a dumpster one night after closing the bar. It was hot. We were classy,” she said. “I used to be the queen of bar bathroom hook ups. The absolute worst was coming out of the bar in broad daylight in the East Village."

Not to be outdone, the regular next to her, who happened to be a bartender from an old school Midtown institution, chimed in: "I once had a chick lean over my bar and say, 'How about you lick my p*ssy with that beard?'"

Elizabeth and I paused and looked at him with raised eyebrows. She continued: "Being a bartender is flirtatious—I used to have regulars back when I was in the industry and I'd always wonder what if. It's just a matter of the moment being right: the stars align, there's a blizzard." She chewed her straw. "A blizzard?" I asked. "I literally hooked up with a bartender and cheated on my boyfriend because there was a blizzard and I couldn't catch a cab,” she said.

"There was a time when I was cl-opening a bar in the city and living way out in Brooklyn and I'd wait to see if any patrons had hotel room keys on the bar—I just really didn't want to pay for cab fare," my friend Kristina said, putting a saison in front of me. "But the real story, I suppose, is my affair with a superhero." She whispered his name and I choked on my beer. "It's actually an amazing story—his agent hooked him up with an apartment next to my old bar. He'd feed me sushi and throw me around because he's, well, a superhero. He was here shooting a series and he'd come into the bar when I worked lunch and order wings and whatever IPA I recommended. We loved each other's company but we initially said that nothing could happen. I mean, he was married. Then we had too many Yuzu Margaritas and he kissed me on the lobby couch—and he's a terrible kisser. The superhero is a terrible kisser! But he's probably the hottest thing I'll ever have sex with...getting thrown around by that man. Ooooo lawd!" My eyes must have been as big as the superhero's resplendent biceps, his prolific pectorals, his—we'll just leave it at that. She sighed.  "No one knew who he was when we were seeing each other. He's too high profile now. I never gave him my number, but he always knew where to find me. He'd call to make sure I was working."

"People fetishize you behind the bar, dude. You know it's true,” another friend told me. “This beautiful woman I met at Imbibe Ball used to come into my bar after we first met.” This particular friend happened to work at one of the foremost cocktail bars in the country. "She would come in and flirt like wild. One night she slid her panties over the bar while I was working! Thank the lord my uniform involved something with pockets. We had this intense, whirlwind romance. She moved, and the last time we had goodbye sex I pulled a muscle in my arm. I had to wear a sling from break-up sex!" He raised his Martinez, "I still have those panties in my closet."

My first bar gig in the city came with an interesting crew of regulars. They would primarily congregate around the end of the downstairs bar, spilling into the serving area where they were able to avoid the theater goers and tourists who ran rampant in those parts. One particular regular happened to not only be young, witty, single and attractive, but he also happened to live right upstairs. It was fairly common knowledge that he'd already dated one of the waitresses. He was a good-natured dude, easy going, and it didn't hurt that he also had a ridiculously adorable dog.

I'm not entirely sure how it happened, but at one point in time, one of my coworkers was carrying on simultaneous affairs with this upstairs dude with the dog, her out of state ex-boyfriend and her live-in boyfriend. I remember one particular New Year's Eve when all three of them happened to be on different floors of the restaurant, seemingly oblivious to each other while she swigged Jim Beam and hyperventilated in the keg room. She'd done a pretty stellar job at keeping the affair upstairs a secret, until one morning she stumbled out of his front door and ran directly into another co-worker of ours who was headed in to work the lunch shift. The jig was up.

After she ended the fling, homeboy made a pass at me to which I replied, "No thanks, man. You've already slept with too many of my friends." I guess some of my other coworkers didn't share the same sentiment; there were plenty more upstairs affairs.

As I was excavating the alcohol-soaked images of the past, I realized there was one friend I had never really talked to about her now decade-old fling with one of her regulars, who happened to be a detective for the NYPD. Lucky for me, she was more than happy to fill me in. "The whole thing was so weird, I was so afraid it would come back and my boss would find out,” she said. “There was this super late night and he was super drunk and he asked me out. I ran upstairs and asked my coworker, 'Didn't he just get married? I can't do that!' And she said, 'Yes, you can, because he's not anymore.' I guess he'd only been married about a month.  Never really asked him what happened. Anyway, I just always thought he flirted with everyone. He was always telling me what a great cook he was."

"So what made you say 'OK,’” I asked. “I mean, I remember him being witty and kind of hunky but wasn't he—” “Like, 10 years older?" She laughed into the phone. "Yeah, he was. I think I was 26 and he was 36/37. I don't know," she paused. "He was sweet and so I met him at a beer garden in Queens. We wound up back at his place, which had no furniture except for this super ugly orange couch—I mean, he'd just gotten divorced. After that, we saw each other every weekend for about five months. Then I went to Germany to study, and he kept threatening to show up and whisk me to Belgium," she laughed. "And you know he was the kind of crazy who would actually do that! After I got back, he went away on a trip to Paris. But the bar was his first stop back after the airport. He rushed right in and kissed me in front of my boss! I got the hot sweats for weeks but my boss never said anything."

"So, what happened?"

"It just kind of fizzled, I think he realized I wanted more than a weekend sex buddy no one knew about. I do think about him. Even though he drank a lot, he was such a nice guy. After sex once, he put on the song from Flashdance and put on sweatbands and spandex—he'd been trying to get into working out. And then he danced around." I could feel her smiling through the phone. “God, it was so not sexy but it was hilarious! And I thought, 'You must really like me if you're willing to embarrass yourself,' and then we had sex again."

Plenty of bartenders use the allure of availability to sell spirits. Have a boyfriend? Not at work ya don't! Live with your lady? Never mention her to the women at the bar. In my experience, those routines don't usually lead to stories that result in anyone’s panties being slid over the bar. But if they do, there’s one of two outcomes: awesome, no-strings-attached sex or heartbreak.

In college, a friend of mine dragged me to a karaoke night on Bleecker because she was "dating the bartender." The "boyfriend" in question seductively leaned over the bar, taking orders from glossy-lipped gals while his female co-workers peddled Jello Shots in their crop-tops. One look around the room and I had to ask, "Have you ever gone on a date with him?" To which she replied, "No, but I meet him after work." “Yeah, yeah but has the man ever slept over?” I gazed at the trio of scantily clad coeds twirling on the stripper pole. "Oh, um no." “You're not dating him,” I informed her. “You're renting.” She paled. I then proceeded to do all the free Jello Shots passed my way.

I'm pretty sure that night was my friend's last hurrah with that bartender—we certainly never attended another karaoke night in that fine establishment. Her stint as a regular there ended, just like that.

Of course, not all bartender-regular affairs end with one of the parties permanently exiting the bar. There's nothing quite like walking into a room and realizing one or more of the people bending their elbows at the bar have seen you naked. Reinstating the equilibrium after doing the deed can be tricky. But hey, maybe you should've thought about that before you gave into temptation while serving that Happy Hour hottie her usual.