Ace Your Dinner Date!

Advice from waiters (and daters) on where to go, how much to tip, and sweet-talking tips that’ll guarantee a great first impression.

By Molly Sorohan

t’s not so often that dinner dates turn out to be those perfectly romantic evenings bathed in candlelight, brimming with meaningful glances and—oh yeah, amazing food to boot. In reality, dinner dates tend to be slightly nerve-wracking affairs full of potentially first-impression-busting decisions: Where should you go? If you get steered toward a bad seat near the kitchen, should you say something or just deal? Who should pay, and how much should you tip the waiter? Never fear: Follow these tips from veteran restaurant employees and real daters and you’re guaranteed to give off a great first impression and be able to focus on what you’re really here for: each other.

Do choose a place you have been to before.
Even if you have only been there for a drink, knowing your surroundings will make you more confident, comfortable, and therefore much more attractive to
Wandering violin serenades or waiters dressed like Elvis will only distract you from the main attraction: getting to know each other.
your date. “The stress of a first date is enough that I don’t want to deal with a completely new situation,” says Brigitte Stanovick, 28, of New York City. Trying a new restaurant can cause date-night anxiety: “I’m loving this place!” you declare confidently to your date before opening the menu and realizing it’s in French. Or perhaps when you’re in a new environment you say, “I’ll be right back!” but then wind up bumbling around for 15 minutes searching for the restrooms. The restaurant could also be too loud, take forever to seat you, or have terrible food—all of which can throw a major wrench in the mood.

Don’t go somewhere too familiar.
If the maitre’d, busboy and line cook know who you are, if you are shown to your “usual table,” if the wait staff knows your drink and your steak temperature, that’s not necessarily a good thing. You may aim to impress, but your date is most likely wondering how often you bring dates there. You may well want to share your favorite haunts, just not on the first date.

Don’t choose a place too close to home.
“If a guy took me to a bar right around the corner from his place, that is the least effort he could possibly put into a date,” says Sarah Gager, 27, of New York City. While your “old standby” may be comfortable, remember that you are not aiming for comfort. You want passion! Romance! Excitement! Also, keep in mind that if you tell your date how conveniently close you live to the restaurant, he or she may assume you intend to end the night back at your place. The place next door may have charm, sophistication, and a fabulous chocolate soufflé, but save it for the third date.

Don’t be afraid to ask!
This rule applies to dates with possible vegans, vegetarians, smokers, non-smokers, spicy-food enthusiasts, wine lovers and sushi haters. Don’t assume that someone will like something just because you do. “I work at a steakhouse and we constantly have to figure out what to serve to vegetarians,” says Isaac Honan, 28, waiter at Manhattan’s Maloney and Porcelli. “There’s, like, two things on the menu that they can order.” Avoid an obvious dating snafu by having the foresight to ask about preferences upfront.

Do steer clear of shenanigans.
Wandering violin serenades, waiters dressed like Elvis, and other forms of table-side entertainment might seem fun or romantic in theory, but in truth they can distract you from getting to know each other. Even if you’ve been there before, a quick phone call or glance at a website may prevent a lot of trouble. “I never knew they had a mariachi band on Thursdays” may be a good excuse, but it’s not going to save your date. “You want to be stimulated by your partner, not over-stimulated by your surroundings,” says New Yorker Veronica Waller, 30. Find a place where both of you will be able to focus on each other.

Do splurge on a good table.
Whether you choose an intimate Old World bistro or a breezy sidewalk café, the one thing you don’t want is to be in the way. Avoid potential jostling, spilling, and apologizing by requesting a certain table when you make the reservation. This is another circumstance in which knowing the restaurant comes in handy. If you haven’t made a reservation or don’t know which table to request, explain that you want a private table, not too close to the kitchen—or one with a view… whatever will make the evening special.

Don’t feel obligated to go somewhere expensive.
While you may aim to impress, you may end up intimidating. “If it’s really fancy, I worry if I’m acting right. I worry if I’m pronouncing menu items correctly and using the right fork, you know? I’m thinking of other things instead of concentrating on the person,” says Meghan Breitzmann, 28, of Cleveland. Opt for a laid-back atmosphere, which will make you both feel comfortable and will nurture conversation. Save the Four Seasons for your anniversary.

Don’t assume anything when it comes to the check.
We know it’s unfair, but even in this day and age, men usually pick up the tab on the first date. But that doesn’t mean a woman should
Do choose a restaurant you’ve been to before. Otherwise it could be too loud or have terrible food or service—all of which can throw a major wrench in the mood.
just sit there and assume that’s going to happen or make a convenient trip to the restroom when it’s time to pay up. Men, it appears, still appreciate when women make a genuine offer to split the bill—and this means you not only reach for your purse but open it (make sure you have cash handy in case he accepts). While he may likely refuse, this gesture shows you appreciated his company and didn’t just show up for the free surf ’n turf. “I like when a girl pretends to take out the pocketbook, and I then say, ‘Oh no, you really shouldn’t,” says Mike Barish, 26, of New York. “It lets me be a gentleman, and I see she’s trying to be polite.” If accepting such largess makes you uncomfortable, try this trick from New Yorker Kate Paulin, 25: “My response will be ‘All right, I’ll get the next one.’ Or ‘I’ll get drinks.’”

Do take care of your waiter.
Tipping says a lot about a person. While throwing around too much money may paint you a showoff, adhering to gratuity standards is a good idea. “I was a waitress for four years, so I always look to see what they tip,” says Paulin of her dates that pay the tab. “If it was anything under 18 percent, it would be a small strike against them.” Figuring the tip is easy: Take the total and move the decimal point one space to the left, and you have 10 percent. Double it, and you have 20 percent. Unless the service has been a nightmare, that 20 percent can be an investment in your date’s opinion of you.

Do be discreet.
Paying or tipping should always be done as smoothly and as subtly as possible. Do not make clumsy, boarish errors such as arguing over how much each person owes (read: you’re cheap), using large bills to pay for small checks (read: you’re showy), or gregariously grabbing the check out of the waiter’s hand to demonstratively pay with your credit card. Such behavior makes people feel beholden and uncomfortable. Just pay the check, move it to one side, and be done with it.

Do plan for the best.
If things go well, then what? Say you’re having an amazing night that you want never to end. Great! Unfortunately, the lights are up, the tables are empty—and the waiters are yawning. It’s time to leave, and nothing makes you look cooler or sexier than knowing a great bowling alley/wine bar/pool hall just around the corner! Now is the time to mention that your former roommate bartends two blocks away to see if your date’s up to continuing the fun. Being prepared can help stretch a good time into a great evening.

Molly Sorohan waited tables at restaurants throughout New York City, including Bolo and Morrell Wine Bar.
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