Tales from Behind the Bar: The Best Worst Dates

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Bars: The quintessential arena for dates both good and bad.

His photos were boyish and cute, he was tall, and he looked a little nerdy.  We had exchanged pleasantries over an online dating app, and set up an afternoon to meet in person.

I met him at a bar, that nervousness sitting in the pit of my stomach that has become an all-too familiar feeling in the zeitgeist of online dating and dozens of first dates with relative strangers. 

The first thing he says to me, as I slide into the bar stool next to him, is a spastic “Just so you know, we’re going to be splitting this, ok?” Not a hello. Nary a nice to meet you. Heaven forbid a friendly hug.

How many of these pairs are experiencing a horrible date?

And that, single men of the world, is how you squash the fluttery butterflies in a woman’s stomach.  He proceeded to be confused about how tabs work, arguing with the bartender. I spent the next hour politely looking at photos of his ex-girlfriends, oddly all of whom were significantly older Korean women, and listened to his musings about how being an administrative assistant at a large law firm was like cat herding. He must have said the phrase “cat herding” 15 times, like a nervous tic, oblivious to the vacant look in my eyes. I remember thinking I would rather die alone with a herd of cats than date this person.

As we paid up (splitting the check of course), the bartender motioned to me to hang around for a minute. After my prince charming had left, the bartender put another glass of beer and a shot of whiskey in front of me and stuck out his hand.

“On the house – I tip my hat off to you,” he said.  “You smiled through that like a champ. It was painful to watch.”

And that got me wondering. Online dating has become a necessary evil for single people today; we self-inflict what were traditionally called “blind dates” on ourselves, except it is suspect algorithms that do the matching, not our well-meaning married siblings or grandmothers. And bartenders must be witness to a lot of these blind date romantic disasters.

So I asked a bunch of them in the neighborhood about the worst dates they’ve ever seen from behind the bar. These recollections were collected over multiple conversations with staff and industry friends,  and sourced from Beuchert’s Saloon, Tunnicliff’s Tavern, Acqua Al 2, and Molly Malone’s. Identities are not disclosed to protect these horrible date whistleblowers.

Maybe Acqua Al 2 should scribble “Beware!” On the upper left corner of their building.

Well, That Escalated Quickly
Acqua Al 2 is a very romantic restaurant; inarguably one of the top spots in the neighborhood for a dinner date with its low, warm lighting and cozy atmosphere.  One late night, two people, clearly on a first date, were the last individuals at the bar. They were sitting by the dishwasher, where the bartender was polishing glasses and idly eavesdropping on their conversation, unavoidable since the entire restaurant was empty save these two people.

The woman asked something that is always a loaded question on a first date: “What is the most serious relationship you have ever been in?”

Hesitantly, he informed her that he was a widower at the tender age of 30, and that he had lost his wife about a year and a half prior in a freak accident (beware, single people: don’t ask this on a first date!)

But that was not the most awkward part of this interaction. Not by a long shot. That was cemented by her response:

“So am I prettier than her?”

The bartender, mortified on humanity’s behalf, and rightly so, fled, not wanting to bear witness to what may be the worst reaction to a personal disclosure of tragedy, ever.

But, there is a happy ending! The bartender tentatively returned to the bar area, only to find the budding couple making out passionately, all over each other. She never did find out what transpired between “Am I hotter than your recently deceased wife?” and the lip lock. 

A Truly DC Date
Our next foray down bad-date lane begins in 2016, the year of a contentious election (you may recall it). One night at Beuchert’s Saloon, a young man came in and awaited his date. The woman arrived, and it was clear from the beginning that these two individuals were at the opposite of the political spectrum – not necessarily a kiss of death in the DC dating scene, but the odds are high; he was very conservative and she was very left of center.

Upon realizing they may not share the same ideals, the woman diplomatically asked, trying to bridge the gap of their political divide, “If you could select one Republican to be the presidential candidate, who would you choose?”

His answer: “Ben Carson.”

Cue Kiss of Death music (although if the young woman could have seen into the future, she may not have been so revolted by his answer).

Needless to say, the rest of the date did not go well, and ended with the lady slipping the bartender a piece of paper – with her number scribbled on it.

You Have a Nice (Gingivitis Free) Smile
One bartender recalled a date where the Romeo opened conversation with an icebreaker about how his family has a history of gingivitis.  This was ostensibly offered as a preemptory defense to disgustingly picking at his teeth with multiple flossers during the entire date.

Be Nice to Wait Staff
It was the day of the Marine Corps Marathon, and Molly Malone’s was slammed. They have a small kitchen, and orders were taking up to 45 minutes to come out. The servers did their best to manage expectations, but one half of a couple learned the hard way that thou shouldn’t protest too much.

A couple ordered a plate of tots. The wife became incensed at the length of time it was taking for said tots to arrive. After being verbally abusive to a number of staff, this woman, well-dressed and decked out with a huge rock on her hand, flagged down a male server, an action her husband would ultimately regret.

The server walked over, and immediately recognized the guy sitting opposite the irate woman. Why?  He had hooked up with him after connecting on Grindr mere days prior. The cringe-worthy, horrified look of recognition on the patron was priceless.

“Dear, calm down, please don’t talk to the staff that way” he pleaded, as the server assured her sweetly that their order would be out soon, cocked his eyebrow at the man and sauntered away.

I believe the woman’s delayed appetizer was the least of her problems.

You Said You Liked Trying New Things
A man met his date at a bar, where the woman communicated the common disclaimer: “I want you to know, no matter how well this goes, that I have plans at 10:15 p.m.” She was carrying a very large tote bag, the importance of which would be revealed later.

As it neared the end of their date, the woman excused herself to the ladies room. The man took advantage of her absence to peek into her gigantic tote bag.  There was a riding crop nestled in it.

Upon her return, unable to restrain his curiosity, he asked “What’s with the riding crop? I don’t think you’re going horseback riding at this hour.”

She admitted she was going to a BDSM happy hour after the date. Surprisingly, she asked him along! If that’s not a sign of a date gone well, I don’t know what is, folks.

Happy Valentine’s Day to all you singles in DC, and good luck out there. May all your dates involve politics, Grindr, and riding crops.