Photo of Kapri Robinson by Darrow Montgomery

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As D.C. bartenders shake and stir your drinks, they’re on double duty as covert navigators of D.C.’s finicky dating scene. Catch them nodding in agreement as you show off your embellished cocktail knowledge; acting with lawyer-like discretion as you bring your third first date through the same bar in a single week; and offering to take over your Tinder account for the night, swiping right as they see fit.

They’ve seen it all, which is why City Paper asked seven female bartenders with 62 years of combined experience to divulge what they’ve learned about dating in D.C. and what advice they have for District denizens trying to find their one true love, or at least a one night stand.

We’re starting with women, but look for the companion column featuring advice and observations from men in the coming months.

Bartenders employ minimal detective skills to discern when you’re on a date.

“They have this nervous look every time someone comes through the door,” says Kapri Robinson, who bartends at Reliable Tavern. “They stare them down and ask, ‘Is that the profile picture I remember?’ There’s over-excitement when they start to talk. Maybe it continues or maybe it completely dies.” 

Colony Club Bar Manager Lauren Paylor agrees. “There’s always that awkward introduction where you see them wandering around the bar comparing face to picture,” she says. “Worst case scenario: People walk in, aren’t happy with what they see, and walk out.” 

Mistakes happen. “There are some funny stories of people meeting the wrong person and then the right person shows up,” says Maxwell Park bartender Niki Lang. The wine bar she helps run is a first date magnet. Daters can doodle on a chalkboard-topped bar if conversation stalls. 

“A guy came in and went up to a girl, which was the wrong girl, and then his correct date showed up and he actually asked the girl he sat next to to get up and move to make room for his date,” Lang explains. “The other girl and her date were laughing it off while the guy and his [new] date had the worst time. It was the fastest I’ve ever seen anyone drink wine. You can tell within a couple minutes if they’re going to go really badly.”

Bartenders commit bad dates, public breakups, and rotten behavior to memory. 

“The worst breakups are often when men believe the woman they’re breaking up with is not going to have an emotional outburst because they’re in public,” says Jessi Weinstein, who currently bartends at Maydan. “The reality is a woman is like, ‘I don’t care you, just really hurt me.’ As a hospitality person you don’t know what to do. The first time I saw a breakup, I was like, ‘Maybe I’ll send her some almonds? A little bar snack?’”

Megan Shaff, a bartender at Seven Reasons, has also worked at Maydan. That’s where she witnessed a breakup that produced a medical miracle. A woman on crutches hobbled into the hotspot to sit down with a man whom Shaff presumes was her boyfriend. 

“They’re not agreeing on anything about the meal, drinks, or their weekend plans,” Shaff says. “Then they’re in a full-on screaming match at the bar.” At one point he tells her he’s done and walks out. “She throws the crutches to the side and goes running after him. We had to chase them down and get a card to make them pay for the meal and return her crutches.” They inquired if she was OK. “We couldn’t stop laughing about how she had suddenly been healed.”

Some people wait for their date to use the bathroom and then bail, according to several bartenders. Robinson tended to two people who seemed to have started their date elsewhere before settling down at Reliable Tavern. They ordered two negronis. When he hit the restroom, she closed out. “I don’t know what happened,” Shaff says. “I asked if she was OK because we’re very protective. She was like, ‘He’s just a dick.’ I was like, ‘I hope you come back,’ as she was storming out.” He finished both negronis.

Many D.C. bartenders are trained to recognize when patrons are uncomfortable or in distress to prevent sexual harassment and assault. Some bars use their own curriculum, others call on the D.C.-based organization Safe Bars to learn bystander intervention techniques. About 25 D.C. bars are active Safe Bars participants. And a recent initiative in Arlington instructs patrons to “Ask for Angela” if they feel unsafe. More than 20 bars are participating in this initiative.

Carlie Steiner works with her staff at Himitsu to closely monitor whether diners are having a good time and remembers some challenging scenarios when she was bartending at barmini. “When you get into those price tiers of barmini cocktails, unfortunately our society has created a dynamic in the dating world where someone feels they are owed more for spending more,” she says. “That’s why I’ve become so diligent for looking out for stuff that seems uncomfortable.”

The ubiquity of online dating has changed bar culture.

Jack Rose’s upstairs terrace was the mecca of Tinder dates,” Shaff says. She previously worked there as well. “Tuesdays you could look down the entire bar and it was all first dates.” 

Shaff believes apps have caused younger Washingtonians to collectively forget how to converse. “They’re not used to talking to someone in real life,” she says. “They’re more comfortable sitting next to each other and texting one another. I’ve seen people sit down and have nothing to talk about, probably because they’ve texted it all. But then they look at each other and are like, ‘Are we doing this?’ Then they walk out and you know they’re going to smash it out.”

“You know so much about somebody before you sit down with them now,” Steiner adds, based on observation and personal experience. “The last few dates I’ve been on I can tell that people have Googled me.” The questions are too specific. Overall, she says, it makes it harder to tell when people are on first dates because couples have already broken the ice. 

Old dating norms are gradually falling away. “You don’t really see guys buying girls drinks,” Shaff says. “No one wants to be approached anymore.” Robinson concurs. “It’s hard now to really navigate how to speak to a stranger without these presumptions that it’s a negative thing,” she says. 

On the rare occasion that someone wants to buy another patron a drink, Robinson has a strategy. She first asks the person on the receiving end if they’d like to accept the drink. “If they say ‘No,’ I tell the person, ‘Sorry, I can’t do that for you,’” she says. “If they agree, I’ll say, ‘Would you like to take it over and say hello?’ I see this situation. I’m watching it.”

The state of forming unions is a little bleak.

“It seems like it’s a bit rough out there,” says Jo McDaniel. She’s the bar manager at A League of Her Own, a new bar for LGBTQ+ women inside Pitchers. “As much as we’re a transient city, it’s a bit incestuous,” she says, recommending that newcomers ask bartenders to dish on whoever they’re crushing on.

“Don’t take a date somewhere you have a lot of history because you will run into people you’ve slept with if you go to the monthly queer girl party,” McDaniel also suggests. “I’ve seen recently broken up people both on dates with other people staring at each other across the crowd because they’re not over each other. Don’t do that.” 

While the queer scene could use a larger dating pool, the heterosexual dating world isn’t evenly matched. City Lab reported in February that heterosexual men have a considerable dating advantage in D.C., where there are 63,000 more single women than men. “It’s definitely a man’s world in D.C.,” Shaff says. “They have the pick of the litter.” 

Some bartenders say they see women giving men second looks when they shouldn’t. Weinstein points to two men who came into Maydan and sat next to two women, one of whom was single. They started conversing. “It piqued my interest because I overheard one of the men tell the women he’s dating someone eight years younger and he wouldn’t be OK dating a girl who is four years older,” she says. “Obviously we know we’re going to a bad place at this point.”

Right before the alleged braggart left, he reached into his pocket, pulled out some paper trash, and set it on the bar between the two women. “I thought it was so bizarre,” Weinstein says. “Then the married woman in the group goes, ‘Oh well, he seemed kind of nice, maybe you should go out with him.’ They just looked at me and I was shaking my head.”

Drinks will cost you, but this advice from bartenders is free

“I think it’s wildly important to advise daters not to hit on the bartender,” McDaniel offers. She’s had people get flirty in front of the person they’re supposed to be wooing. She also cautions would-be daters not to plan on a romantic connection at 9 p.m. on a Friday. “That’s going to be loud loud and dark dark,” she says. “I do not recommend high traffic and high volume times where you’re trying to focus on another person, getting a drink, and navigating a crowded bar. It’s not romantic. Happy hour is a great time to date in D.C.”

Robinson warns against politics as a first conversation topic. “That starts to get into sticky waters when two people meet and realize they don’t think alike … Being in this area makes people think they need to be politically savvy and come out with guns blazing. I want people to sit, chill, drink, and talk about who they are as a person and what they enjoy doing.” 

Lang encourages daters to mingle. “Try to have a good time and relax because the dates where people are having fun and playing and joking around are always the best,” she says. “The people that come in on dates and end up talking to people around them and being engaging in general end up better than the ones that are more intense.” 

“Don’t get nerves on a first date,” Steiner says. “It’s important to remember your value. You are assessing that person; you’re not there to be assessed. If everyone thought that way it would be a much more comfortable experience. Emotionally healthy human beings are attracted to confident people.” 

Robinson echoes Steiner. “Be yourself and be confident in who you are,” she urges. “Be patient with new people. When you’re first meeting someone, be a little bit open and aware that the person is going to have new thoughts and new ideas. Sometimes people don’t have the patience for one another anymore. I think that will help you get past the first date.”