I'm A Waiter Who's Seen It All And Here's My Advice To Men For The Perfect Dinner Date

by Moshe Schulman

A man sits across from his date at the table. They’re getting the initial chit-chat out of the way. A few minutes pass and the food and drink menus are still covering their plate settings. When the waiter comes to take their drink order, naturally, they’re not ready and the man asks for more time.

The waiter returns 10 minutes later and they’re still not ready to order a drink (this will happen for the food course, too). What’s the big deal? Two people are getting to know each other.

True, but this is valuable time being wasted. You’re being interrupted by wait service, and your date would like you to take charge and order some damn drinks already.

As a waiter in New York City for the past five years (I’ve been in the restaurant business for over 10 years), I’ve served hundreds of daters, and there’s one thing that consistently stands out: a good majority of men are not that good at this whole dating thing.

I don’t mean that their personalities or looks are a hinderance; I’m talking about their ability to order food and drinks without coming off as indecisive and lacking in confidence.

I'm talking about their ignorance of some technical steps when ordering that could make their dinner experience a lot smoother, like accelerating the initial nerves/awkwardness to ordering drinks, having a good dinner, and maybe even an after dinner drink.

Below are some tips/suggestions to the fumbling men out there.

Research the restaurant/bar where you’ll be taking your date.

This allows you to take a sneak peek at the food and wine menu so you’re more prepared when the waiter arrives. Also this gives you the time — without the pressure of your date staring at you — to be prepared to make decisions when it’s time to order.

Being more knowledgable about the menus also gives you more options to offer to your date.

Researching the restaurant/bar will also inform you whether there’s a reservation or walk-in policy and what time the restaurant closes.

Before choosing a restaurant/bar, ask your date if she has any allergies or dietary restrictions. You don’t want to take someone with a gluten allergy to an Italian restaurant, etc.

Always have a back-up restaurant/bar.

Sometimes the restaurant you picked to meet at is walk-in-only and it’s packed or, at times, and this has happened to me, the restaurant is closed for a private event.

Nothing conveys confidence and decisiveness more than having a Plan B. So have a back-up restaurant/bar that’s in the area or a quick cab ride away. Don’t get stuck searching for a bar on Yelp while your date stands there.

Order drinks (and food) as quickly as possible.

The first few minutes you’re sitting at the table is time to settle in and talk a bit, but don’t forget that you’re both nervous and delaying ordering a drink only continues the awkwardness.

When you order a drink, it frees up the nerves between both people. It also helps you get the night moving along to a good conversation.

So after a few minutes of chatting (definitely after the waiter has welcomed you and asked for the first time if you’re ready to order drinks) I’d recommend you suggest to your date that drinks and food should be figured out so you could continue the date without interruption from the restaurant staff. Simply put:

Let’s figure out drinks and food now so we could continue talking without being interrupted.

Don’t have small-talk with your server.

Always keep in mind that your date wants to get to know you; all the other fussing around takes time away from the two of you conversing.

So get good at cutting out the bullsh*t banter between your bartender/server like: So how many years has this place been open? Are those candles real? What’s your name? Are you (insert random ethnicity here)?

Stop asking irrelevant questions when ordering wine.

When you’re ready to order wine, don’t ask the waiter about four different grapes and the specific regions of the wine if it’s not relevant to you making a decision about the wine.

You asking those questions (most likely because you’re nervous) is not impressing the girl; it’s quite pretentious actually.

If your well-versed in wine, you’ll know the answers to those questions anyway. So if you’re not a sommelier, keep it simple: “I’m looking for a red similar to a Cabernet” or “Can you recommend a white that’s similar to a Sancerre?”

Avoid the dull and painstaking “Are you hungry?” conversation.

Abridged version of that conversation:

“What do you like?”

“I don’t know. What do you like?”

“I’m not that hungry.”

“Do you like ______ (insert random item off the menu).


“You sure?”


Awkward silence.

I recommend ordering food and drinks at the same time. If you can’t do it at the same time, then at least be ready to order food when your waiter comes back with your drinks.

That time in between is for you to decide your food order. Remember: You’re on a date to get to know each other, not to spend an hour looking at menus and debating what to order.

If your date says she’s not that hungry, believe her. Don’t proceed to order eight dishes on the menu. Even if your date is hungry, don’t order eight dishes on the menu.

You probably won’t finish half the food you eat; either you’ll be too full after the first or second course or your table will be cleared to make room for the next course. Order conservatively— you could always order more food.

I recommend a three-course meal: an appetizer, a mid course and an entrée to share. Before ordering, make sure your date is comfortable sharing.

The best way to figure out what to order without the glib banter is to communicate to each other what pops out at you on the menu. From there, you could come to a consensus. Don’t order for your date, order with her.

“The Orecchiette with pork ragu looks really good.” “Yeah, I was looking at that, too.”

Done. Simple. Easy. If she’s not really into pork then recommend another dish that you prefer until you’re both on the same page. I’d recommend echoing back to your date what you’ve picked out. This assures her you were listening and that you’re both expecting the same dishes.

When ordering food, be clear with your server how you’d like your food to come out.

You don’t want all your dishes arriving at once so order as follows:

“For appetizer or first course...” “For our mid course we’d like the...” “For entrée or third course...”

Ask your server to slow down your ticket.

Some servers are perceptive and will recognize that you’re on a date and they’ll take the initiative to slow down the speed at which your courses arrive.

It all depends on the type of restaurant you’re in (casual or fine dining, etc). But in any case, after telling your server the order, I’d recommend asking the waiter to slow your ticket down (especially if you have multiple courses).

Simply say, “Can you please let the kitchen know to slow down our ticket/table?” This not only gives you time to get to know your date without feeling rushed while you eat, but this also clearly lets the waiter know that you’re not in a rush and that you want space for the remainder of your stay.

Always have a go-to late night spot.

Having a late night drink spot is key to moving the night along and keeping the night interesting. People get restless; after a few hours in one restaurant, they want to move elsewhere.

It’s even more important to have the late night option if the restaurant you met at is closing and you’re still having a good time with your date.

The moments after having dessert (or not) provide a great opportunity to suggest getting another round of drinks at a different location.

Simply put: “How do you feel about getting another drink somewhere else?”

This also conveys confidence and spontaneity. More importantly, this is a great way to gauge whether your date is really enjoying herself. If she wants to go out for another round then things are probably going well.

Stop being vague when paying your check.

Don’t hide your credit card or cash in the flap of the check presenter or, if it’s a clipboard, don’t turn it upside down.

The server needs to see that you’ve either put cash or a credit card down. Your server won’t interrupt your date if either is not visible. So make sure the card or cash is sticking out of the check presenter or, if it’s on a clipboard, face it upright.

If you’re paying in cash simply say, “No change” or “May I get (insert amount) back?” This avoids confusion or miscommunication. Once your bill is settled, it’s time to move on to the late night spot and/or hopefully to a second date.

Don’t be the lingering couple.

Yes, you’re having a good time, but you should also be aware of your surroundings. If you’re the only ones left in the restaurant, it’s probably time to move on.

Unless you’re cheating on your wife. And we know if you are... corner table or lounge chair in the back and heavy petting; it’s already been four hours and you haven’t gone home. We all know.

Photo Courtesy: Paramount Pictures/Wolf of Wall Street