Author Amy Lynch
Author Amy Lynch

My question is – why the heck not? I suppose being single and living alone for nearly a decade before I got married at age 35 conditioned me to be comfortable in my own company. Nearly all of my friends married and had kids long before I did, so I grew accustomed to them not being able to drop everything on a whim to come meet me for a spontaneous (or even planned) drink, meal or movie. It got to the point where if I wanted to do something and no one was available to join me, it became a matter of either going alone or sitting home seething because I was missing out. I became quite adept at solo dining, taking in the occasional concert or trip and I grew to relish and enjoy it.

So, in Chicago I decided to treat myself to a really posh meal on my last night there. I had originally planned on a juicy steak, but changed gears at the last minute and opted for Italian. I asked the concierge at my hotel for a recommendation – somewhere I wouldn’t feel like a sore thumb without a companion, but somewhere I could partake in a great meal and a glass of wine. I took his suggestion and caught a cab to a place called La Madia.

La Madia was a little trendier than what I usually go in for, but classy and the staff made me feel welcome. I was seated at a two-top near the window with a view of the gas fireplace and bustling bar scene. True to the concierge’s word, I didn’t see any couples on dates, just happy hour groups and a few Sex-and-the-City-style duos and trios of single women out for drinks, apps and gossip.

The server made it his mission to keep an eye on me and keep me happy, making recommendations and checking on me just frequently enough to see how I was doing. He did this more often than his other busier tables, I might add. The wine he suggested was fabulous, and the gnocchi with sausage and spinach in a brown butter sauce divine. The dessert was the high point of the meal, though – some kind of outrageously rich chocolate cake that was sweet but not too sweet, dusted with powdered sugar and topped with crushed pistachios. All in all, a lovely dining experience. I happily paid my bill, tipped big and left feeling on top of the world.

Here’s the thing about dining out alone – it forces you to slow down, take a deep breath, and just be in the moment. No one’s asking you to cut up their meat or converse about how you spent your day. It’s uninterrupted, quality you time. And really, couldn’t we all use a little more of that? If you can resist the urge to crack open a book or magazine, it makes for excellent people watching and eavesdropping opportunities as well.

My tips to pull off a successful solo restaurant visit:

• Firstly, dress well. There’s an aura of mystery surrounding women who dine alone and like it. Let people wonder what your story is. Are you a foreign expatriate in town on business? Perhaps a food critic? An up-and-coming television star eager for a few incognito minutes away from your entourage? Just don’t wear sunglasses indoors. Unless you’re in Los Angeles, which is the only place you might possibly be able to get away with it.

• Adjust your attitude. It’s all about confidence. If you look and act like a pathetic loser who has to eat alone because you have no friends and no life, that’s what people will think you are! Suck it up and embrace a short respite of solitude, for God’s sake! Are you telling me your husband and kids can’t live without you for an hour or two, and vice versa? Come on! Get over yourself!

• Work the situation to your advantage. Sometimes it may even buy you some special treatment. You don’t have to be overly friendly, just smile and act coy. I ate dinner alone at the hotel bar my first night in Chicago, and the bartenders swung me an extra-full glass of wine and plied me with free snacks the whole time I was sitting there.

So I issue a challenge to bold women everywhere – demand a free night from your significant other, throw on a dress and some lipstick and take yourself out on a dinner date sometime soon. Scared? So what! It’s good to do things that scare you sometimes, just to prove you can. Pick somewhere nice. Don’t just slum it at a fast-food place, wolfing down fries as fast as you can to get the experience over with. Slow down, unwind and sit with yourself for an hour or two over a delicious meal and a drink. And don’t skip dessert. Do it! Tell ‘em I sent you.


A freelance writer and independent caterer, Amy Lynch currently lives in Indianapolis with her husband and toddler. Her favorite travel destinations include Ireland to see the in-laws, Paris, Amsterdam and California wine country.