Good Habits: The Case For Dining Alone

Some of us really enjoy our own company, and I am one of them. I have a naturally independent spirit and often dine out alone. It's not about making a statement, but simply that after a day of meetings, emails and texts, I need to pause and process the day.

I embraced solo dining at the age of 21. When I had my first business trip to Milan for fashion week, I stayed in the 5-star Principe di Savoia hotel. When I went down to have dinner in the restaurant, it was of course, full of influential people from the fashion industry and businessmen.

I went down alone, fearless. But the maître d gave me a table for two. After I explained that no one was joining me, he asked me if I was staying in the hotel. I thought ‘oh boy, he thinks I am a hooker’. He called reception to check my name and saw that I was staying in the hotel, and in a suite no less. He then looked at me again with a puzzled face and sat me not in a quiet corner, but at a table in the middle of the room. I felt a thousand eyes looking at me. I sat poised and would not take my eyes off the book I was reading to make certain I appeared super sure of myself on the outside, even when on the inside, I was dying.

At one point I looked around and could see the judgement and presumptions in people’s eyes. That couple feels sorry for me. This man eating alone in the corner will send me champagne because he thinks I am a hooker. That young group of fashion people on the other side are wondering why I am here alone. Did I break up with my boyfriend? Am I looking for an adventurous night? Am I new to fashion? Was I ditched by a friend who had other plans? And so on.

Before I knew it, I realized the restaurant was almost empty with the exception of a man who sent me a glass of champagne in hopes that I was a hooker. I went over to him to say thanks for the glass, but unfortunately I don't drink, I want to be alone, and I would love it if he’d stop staring at me as if I was his dinner. By the time I left, I had a high. I felt super confident and had finally managed to read the book with focus.

Thanks to that evening’s performance, I gained the respect of the maître d and hotel management. When I returned to Milan in the many fashion seasons that came after, if anyone wanted to approach me, they made sure that I was left alone.

I was lucky to have this occasion to kick any fear reactions to the curb, as well as the type of personality to do so. And now that it feels perfectly natural to me, I wonder why so many people, particularly women, resort to eating in bad company rather than no company.

To a degree, the media and entertainment industries have stigmatized doing anything alone, such as going to movies or attending weddings without a date. This is always the ‘sad’ moment in a film or show.

And there is also a cultural element. In North America, particularly in progressive areas such as Manhattan, the high-powered professional having lunch alone (with the ubiquitous salad and Pellegrino) is seen as glamorous and cosmopolitan. North Americans, naturally a lot more individualist, have embraced dining out alone while Europeans, particularly from heritage-rich countries such as France and Italy, have created lunch and dinner to be social occasions.

After I mastered dining alone, I tackled taking a whole vacation solo. And as before, after I forced myself to go, I returned with a sense of calm and fullness that couldn’t have been acquired otherwise. Sure, I had some uncomfortable moments, but in working through them I realized just how much I could be there for myself.

However independent you are and whatever side of the Atlantic you’re on, I encourage you to take yourself out for dinner. The type of self-assuredness you’ll gain will yield rewards in all areas of your life. The more resistance you feel around the idea, the more important it is that you book that table for one. Just remember to decline drinks from strange gentlemen.