How To Dine Alone In NYC

Judging from my sunny, outgoing disposition most people wouldn't guess that not-so-deep down, I'm a bona fide loner. If I don't spend quality alone time, a sense of stress and suffocation takes over. I'm a social butterfly by day and a broody crab that crawls back into its shell by night.

Seeing movies, shopping, even attending social functions: I actually prefer to go it alone. Sit me down at a bar by myself, I've no qualms. I'm bound to make friends with whomever's next to me or mixing the drinks. But, there's one thing I've been too timid to try: dining solo.

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To me, eating alone at a sit-down, white table cloth restaurant usually means one of three things: you're traveling solo, you're a business gentleman, or you lead a life of leisure (and money). Heck, it's expensive to eat out. Salads brush up against the $15 mark and cocktails can run you $12 or more. So, it's an investment I usually use to spend quality time with those I love. Why would I dump so much cash treating myself to an activity that's best when shared?

Well, I also have an obsession with conquering my fears — and, silly or not, I was afraid to sit opposite an empty chair. So, I decided to take myself on three real dates. Not a coffee hangout or a trip to Shake Shack (although that is a good evening in my book); these would be places with wine lists and steak on the menu. The catch? I'd be going sans iPhone. I wouldn't even put it on the table to feel its comforting presence. How hard could it be?

Turns out, very.

On a Friday, I'd taken the day off to spend with visiting relatives and opted for a late lunch on the Upper West Side while I awaited their arrival. Wearing all black and my favorite thrifted straw hat (my friends call it my Vincent Van Gogh look) I felt more than a bit pretentious. There were several other solo diners (all male) on the patio. Who were these guys dining at 3 p.m., anyway? I kept my sunglasses on while munching my Caesar salad. The hovering attention of the waiter made me nervous. By the end, I felt falsely grown-up, but weirdly proud I had done it.

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The second adventure was a Monday night at a French bistro in one of my favorite neighborhoods in Brooklyn. I'd been many times before and knew what to expect — quiet ambience, cafe music, and affordable dishes. This time, I took a journal to sketch out a longer essay I'm working on. I ordered the seafood pasta special. Channeling my best Oprah disposition, I put down my fork between each bite and concentrated on the flavors in the pinky cheese sauce. It was exhilarating. After leaving, I felt refreshed and full (I didn't have to share the complimentary bread basket, after all). It was getting easier.

For my last attempt, I upped the game. No books, no journals, and a fancier locale I'd never been to. "Table for one," I said slightly more naturally than the first two times. I sat for an hour, during which time I felt more out of place than ever, though no one seemed to notice me. By the end, I felt in my own bubble inside the bustling, noisy space. I asked myself questions, I let myself think about nothing. I was at ease. It was a really good date.

On the three dates with myself, I was able to pinpoint the origin of my solo dining woes. First, it came from a paranoia of being judged as a sad, lonely girl (which I am not). Putting myself (and only myself) out there, alone, made me feel vulnerable and exposed to everyone else's presumptions. And, being stuck at a table with my inner monologue was just as frightening. Much like when I try to meditate, my brain entered freeze mode. Staring out at the street, past the 10 other tables filled with couples, I finally felt a wave of calm that let me accept my self-awareness. Sure, I still prefer dinner with my fabulous friends — but being alone can feel pretty good, too.

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Keep reading for all my tips on having a hot date...with yourself.

Go To A Cafe
Picking the right place is key. Never sit down somewhere where you'll feel out of place and uncomfortable. If you're like me, you'll feel more at ease in a smaller place. Anywhere trendy, hard to get into, or overly noisy is a no-go. French bistros are usually warm and inviting, and so is any place decorated with sofas.

Choose A Weekday (But NOT A Friday)
On a Monday, Tuesday, or Wednesday, you're likely to see more solo diners around. Safety in numbers, right? The rest of the week will guarantee loud, celebratory groups of friends, and couples. And, for a first-timer, this can be distracting, annoying, or make you feel especially conspicuous. (Of course, no one's judging your lack of dining company as harshly as you are.)

Sit Near The Window
Bistros with outdoor seating are ideal — they have views to let your eyes roam while your thoughts wander. If it's inside-only, go for a window seat so you can enjoy the scenery and your own company. Staring at another table, especially when it's seated with a couple on a date, can be distracting...and awkward.

Truly Treat Yourself
Go for the steak, the truffle fries, and the cheese-stuffed peppers — indulge. No need to be shy, you're romancing yourself, after all. Approaching the experience as a meditative activity to spend time with yourself is key to making it enjoyable. If you're really enjoying yourself, you'll stop worrying about being awkward.

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Bring A Book
A really good one. One that'll make you laugh out loud (anything by Wodehouse should do the trick). If you feel weird or even guilty about being alone, consider this a time to really dive into that read you've been dying to crack open. Feeling productive should nip that in the bud. Journaling is another fantastic use of that alone time you never seem to have enough of.

Make A Mental Thought List
On my third excursion — the one without technology or reading material — I felt completely exposed. My hands awkwardly moved from wine glass to water tumbler to my neck. How ridiculous. Did I really feel so self-conscious? It occurred to me that this was almost meditating. I was alone with nothing before me but a glass of Pino & Toi, and my thoughts. What was distressing me of late? What did I have to be grateful for? Who should I be loving more? What were some goals I had for the next month? I went through a kind of mental accounting that was not my typical daydreaming. It challenged me to get my priorities straight. And, by the end, I swear I was breathing easier.