A Beginner's Guide to Dining Alone

"Seat for one at the bar" is my love language.

My favorite scene from “Home Alone”.

This post is dedicated to a friend who asked me a very long time ago for advice on dining alone. Happy Valentine’s Day.

I’ve long held the belief that dining and cooking with another person is a more intimate activity than sex. And while this post isn’t about sex, I have to the break the ice with something because dining alone is (in my opinion) an even more intimate activity. Going to a restaurant and eating alone can feel like staring at yourself naked in the mirror—the perfect breeding ground for insecurities and intrusive thoughts. And while this could be a post about finding inner confidence by defying social norms, and letting dining alone be a radical act of self-love, I actually think that dining alone ought to feel like open heart surgery, like sitting with your shadow.

Like sex, the first few times should be awkward. Your self-awareness should be hitting nuclear levels of humiliation and indecision. And for good reason! Dining solo is a definitively lonely thing to do. Learning to be in your own company is one of the many great lessons of adulthood and often avoided by many. Just remember, loneliness and solitude are two very different things.

If you’ve failed to make it out the door because of questions like:

What should I wear? Where should I go? When is the right time? What should I be drinking, eating? Where is the best place to sit? Do I bring a book?

Then this guide is for you.

---

I fell back in love with dining alone after a breakup. When you’re emotionally and mentally depleted, the last thing you want to do is ask someone whether they want the spaghetti or pappardelle. Like, who gives a fuck?

Dining alone felt restorative and sometimes even profound. It was a retreat from repetitive conversations, Slack notifications, and the worst question to have ever existed, “How are you?”. Walking into a restaurant alone, without a reservation, ready to hang up a mental ‘Do Not Disturb’ sign became my weekly routine.

Now, I don’t know what your situation is, but if none of that is relatable, then I want you to think of your favorite movie. Think of the protagonist. Now think of your favorite movie 3/4 of the way through when the protagonist reaches the climax of the plot and suddenly feels a renewed sense of purpose. Fast forward to that part. Great, now stop there and copy + paste that feeling into your brain. Do you have it?

Step One: Getting Over Yourself

Before you bring your whole being into someone’s place of work (in this case, a restaurant), get over yourself. Another belief I’ve long held is that the energy you bring into a restaurant is what you’re going to get in return.

Divorce yourself from any expectations of what the experience should be like. Do. Not. Romanticize. Don’t even look up the menu online. Don’t go to Instagram and creep on photos. Expectations gas up your ego, and your ego is a terrible dinner companion.

I wish I could insert an image of someone pulling their head out of their ass because that would demonstrate this step more effectively than any point I try to put together.

Step Two: Dressing for the Occasion

A good outfit is like armor. Dressing the part is essential, and knowing you look good makes the rest of this a lot easier. Wear something you look good in, but don’t have to think too much about. Personal style is a completely separate rant, but I think it can be boiled down to showing up for yourself — and that’s exactly what you’re about to do.

Tip: I keep a mental list of ‘without fail outfits’ that I can always reach for because they never fail me. I feel good in them no matter what or where or when.

Step Three: Logistics

This is the easy part. Going to a restaurant alone, especially in a city like New York, is a strategically advantageous decision. Just like the saying, “Fortune favors the bold”, New York City favors the lonely. As a party of one, you can get a seat almost anywhere, but you’ll more than likely be at the bar.

The bar is where you want to be, especially if you’re new to dining alone. Unless you’re going to a bar (not a restaurant), then you’ll be strategically out of everyone’s view. Plus, a well-intentioned restaurant will have the bar set aside for first come, first serve walk-in’s.

Should you make a reservation? Sure. But I would only recommend solo dining at a 2-top for intermediate or expert-level solo diners. If you think of tables in a restaurant like a high school cafeteria, sitting by yourself is a power move, but it also places you in thick of everything.

Step Four: Showing Up

Timing, in general, is fickle. If it’s a busy night, the best times to walk in are right at open or at the eve of a turn. Restaurant seatings circulate in 2-hour intervals, so if the restaurant opens at 5pm, that means the first turn is at 7pm (peak hour), and the second turn is 9pm. Walking in 15 minutes before or after a turn gives the host to sort through no-show’s and last minute cancellations, increasing your odds of snagging a table on a busy night.

However, my recommendation would be to fly under the radar on a Tuesday or Wednesday night. You’ll be surrounded by a lot of innocuous parties like awkward first dates or catch-ups with coworkers. It’s the ideal time to get your feet wet before you try something bigger.

Step Five: Ordering

Okay, so you’re seated, now what? Order a drink. Do not be a solo diner that only drinks water. A glass of wine, a martini, a mock tail, a cup of tea… just get a drink. The first drink order lets the staff know what your MO is, almost as if you’re sending a message. My perfect order is to start with a martini or glass of white wine to whet my palate, followed by a glass of wine that pairs with my meal.

When I was a kid, I always thought that becoming an adult with a job meant that I could eat whatever I wanted whenever I wanted. And while that’s partially true (budget permitting), I think that’s the mindset you want to enter the meal with. Go through every section of the menu, take stock of what you’d like to try, what you have had before and know you love, and what you’ve never heard of. Get something from each category. You can break that down by appetizer, entree, and dessert, or—if you’re unhinged like me—you can order 3 different entrees.

Step Six: Existing

This is probably the most uncomfortable part. Just existing alone. This is where bringing a book is handy. Books also end up being conversation pieces with the folks next to you, so keep that in mind if you’re going to bring a book. If you need to cope by doom-scrolling on your phone, that’s fine too. Actually, wait, no. Don’t doom scroll. Besides a car spontaneously crashing into the restaurant, whatever’s waiting for you on your phone will be the first thing that ruins your night.

Simply existing in a crowded room can be a very isolating experience. However, I’ve always found it to be very freeing. No one is paying attention to you, and the only people that are are the ones that are paid to do so. Everyone around you is so wrapped up in their own lives that even for the few seconds they might see you, they don’t really notice you. When you dine alone, you pull off the magic trick of vanishing in plain sight. That seat you’re taking up is yours for the next few hours, but it won’t remember you when you leave.

Barring any weirdos, in the event someone should notice you and try to strike up conversation, take it. Engage in small bits of conversation that remind you you’re in a shared space. Plus, it’s nice to make a new, temporary friend every once in a while. Enjoy your meal, tip generously, and get on with life.