Tables For Two

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A waiter's recap of five dinner dates, from romantic to disastrous.

By my best estimate, I was on fourteen dates last week, with a very eclectic group of folks: men and women, gay and straight, ranging in age from about nineteen to fifty-seven. And it was a pretty quiet week. Now, nobody blushingly asked if I "might like to have dinner" in the office elevator, or shyly met my gaze in the skincare aisle at Whole Foods. Rather, as with a priest who marries nine women on a busy Sunday, my involvement was strictly professional. I'm a waiter, and an uninvited participant in just about every date you've ever been on. Here are five of the most memorable dates I saw last week — and how they looked from behind the apron.

1) "Thanks so much for coming"
He arrives alone and waits at the bar, not drinking. She peers through the front window before coming inside, and then they shake hands like Japanese businessmen. It's eight o'clock on a Saturday night; they're officially on a first date.

It's obvious that they don't know each other very well. These aren't two old friends who finally took the plunge; more likely, she was set up by her Pilates instructor. From the moment I go over, the mood is tense. Unfortunately, he seems to think that to impress her, he needs to act like a modern-day Don Draper, saying things like "A glass of champagne for the lady," and opting for non-verbal waves and nods over good old-fashioned may-I-please-haves. Even in this day and age, guys like him are surprisingly common. Although they're not guaranteed to be straight or male, they are guaranteed to be wearing too much hair product and ostentatiously pricey footwear. Tonight is no exception.

It's the most fun part of my job — except when I get to use the fire extinguisher.

The Pros: Work-wise, these guys are easy; they want to be left alone. He's trying hard to be witty and fresh and chew with his mouth closed while still laughing at all the right places. She's focused on not getting drunk, spilling sauce on her top, or having a repeat of what her ex called "the hiccup fiasco." Neither has time to give a shit if their water glasses stay totally full. 

The Cons: Unsurprisingly, Don flags me down with a few unreasonable requests — first for freshly squeezed lime juice, then for "extra cumin." The upshot is I get to say no both times, which lets them bond over what a dickhead I am, and saves me from having to juice a lime. Each time I have to interact with this table — to clear a plate or suggestively leave the check — it always feels like an interruption.

The Tip: The high end of normal. Don Draper doesn't stiff his waiter.

2) "I know it's only been three weeks, but I think she might be "The One." 
They're smiling, they're giggling, they're bursting with joie-de-vivre. Or at least joie-de-getting-laid-on-a-regular-basis-for-the-first-time-since-that-bitch-Cynthia. Jim's been coming in for a year — he's one of the few regulars I know by name — and he always drinks beer. Tonight, when I ask what they'd like to drink, they grin and practically shout "Barolo!" Before I say anything, his date asks me if I can believe "this guy didn't like big Italian reds until last week when I took him to Crispo?"

Jim chimes in, "And now we totally couldn't live without it!" Next time I pass, he's clutching that glass of red wine with a dopey grin, and dreaming of a honeymoon in Naples. 

The Pros: This table is pretty much the best my night gets. Jim and his date are infectiously happy, overly friendly, and totally forgiving. In their eagerness to show each other off, they're very open, sharing anecdotes and asking questions, which not only makes the hours go by, it's pretty much the most fun part of my job — except, of course, when I get to use the fire extinguisher.

The Cons: At times when I've been single or recently heart-broken, tables like this have been bitter reminders of everything I'm missing out on, causing emergency cigarette breaks and ill-conceived text messages to ex-lovers sent furtively from the wait station. Also, this couple's exuberance interrupts the mechanics of dining. They go in for quick kisses while ordering and gaze into one another's eyes endlessly while their untouched dinners get cold. And when I return to drop their check, they're making out shamelessly, in the weird but common belief that because they are sitting and I am standing, I cannot see them.

The Tip: High to excessive, Jim's tip says, "I'm leaving you an extra twenty because the world is beautiful. And I'm about to get laid."

Crying in Restaurants, with Sarah Hepola – One writer remembers her rougher dinner dates.
The Ten Sexiest Chefs
My First Time – "I was a runner, bringing food from the kitchen. She was a chef."

3) "Mom, Dad, I'd like you to meet…"
They say your relationship with your parents sets the tone for your future romantic encounters. Which means meeting your boyfriend's parents is like having dinner with his craziest ex-girlfriend. Tonight, that British guy and his girlfriend who lives down the block come in with Mum, Pop, and younger brother. I smile when I see them come in, since they're familiar faces and usually chill. And then I remember that no one is "chill" on a date with her boyfriend and his familial unit. Last week, she was a friendly regular who remembered my name and gave me a chummy slap on the shoulder on the way out; now she's waving the empty bread basket at me with a look of panic.

After they leave, I make a mental list of people I know who are happily divorced.

The Pros: At least at the beginning, all are trying really hard to be on their best behavior. Because Mum and Pop are on board, they order better wine, a bigger dinner, and dessert with coffee, all of which are good for my bottom line. 

The Cons: After initial pleasantries, it's time to get to the serious stuff, and tensions inevitably arise. If you don't think that sounds like a big deal for the waiter, you've obviously never tried to inconspicuously clear plates in the midst of a "You never told us she wasn't Catholic" conversation. And, depressingly, the old British patriarch picks up the check, which would be fine, except that the conventions of tipping have changed since 1971. 

The Tip: See above. Two buffalo nickels and a Werther's Original. 

4) "How was your day, dear?" 
They sit and scarcely glance at the menu before ordering, each for himself. They're named Eric and Scott and I'm pretty sure they're bankers or consultants or something. It's 7:15 on a Tuesday, and there is a hardly a moment during the meal when one of them is not idly flicking through his BlackBerry. Two years ago, they used to have long, lingering cappuccinos after dinner and then make out like puppy dogs by the bathrooms. Now they wave off dessert menus and brusquely depart the minute they've finished eating. In fact, this date hardly counts as a date. Rather, it's the obligatory satisfying of hunger before bed — a ritual whose prevailing theme is boredom. 

The Pros: On busy nights like tonight, Scott and Eric are a much-needed respite. They couldn't be easier; they know exactly what they want, and have no requests except that it be delivered to their table reasonably quickly with a minimum of fuss. No pre-dinner cocktails, questions about wine, or long, heart-felt conversations over a shared piece of cake. Instead, they're out the door in less than an hour.

This is basically just a display of bad things happening to other people.

The Cons: Easy though they might be, these guys also lead to heavier-than-usual after-work drinking and all-around unpleasant ruminations on the state of humanity. Is this where we all end up? After they leave, I put Billie Holiday on the iPod and start making a mental list of all the people I know who are happily divorced. 

The tip: Normal, regular, fine, uneventful. Just like life. 

5) "I'm sorry to do this the day before your birthday, but…." 
Tonight, dinner is full of surprises — at least, for me and the poor balding bastard at table six. I'm pretty sure his wife walked in with a plan. Things start out chipper enough, the tone gets a little more serious after they order, but it's not until they've eaten that it really blows up and I'm whispering "Careful with six!" to my coworkers. A minute ago, they were a ho-hum married couple on a date. Now, they are "the break-up table." There are harsh whispers, periodic shouts, and desperate pleas. And one really epic line: as I pass, he taps my shoulder and says, "I'm going to need another round, and apparently, a divorce lawyer."

The Pros: Few, unless you're a sadist, since essentially this is basically just a display of bad things happening to other people. For those among my colleagues who enjoy the odd soft-cover romance novel, there is an element of pleasure. They peer out from the back room, eavesdropping and taking sides.

The Cons: After the bomb is dropped, I don't really know how to proceed. Can I ask if they'd like dessert, even though she's obviously crying? Do I need to clear that steak knife off the table to avoid aiding and abetting a homicide? And after she's stormed out the door, should I encourage him to run after her, or just send him another whiskey?

The Tip: High, I anticipate as he leaves, since people usually over-tip after making a scene. Or — hang on a second — nothing, since out of grief or misdirected spite he took both copies of the credit-card slip with him.

Crying in Restaurants, with Sarah Hepola – One writer remembers her rougher dinner dates.
The Ten Sexiest Chefs
My First Time – "I was a runner, bringing food from the kitchen. She was a chef."

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