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.

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.

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.

FIND MORE
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."