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Answer by Sheila Christine Lee:
It can be really, really fun.
Background: I hated eating alone. I've gone out of my way to avoid eating alone, because it makes me feel awkward and extremely self-aware. I packed a salad spinner on a self-cation in case if I couldn't handle eating alone in a restaurant. By the end of that trip, I had eased myself into eating alone (mostly sitting at the bar), and it wasn't nearly as bad as I thought.
But really fine-dining alone? Table for one at a dress-up restaurant? Crazy talk. I've been extremely lucky to enjoy a few incredible fine dining experiences with close friends, and attribute much of the meal's enjoyment to derive from the company surrounding me.
Until March 2013. I'd secured season tickets to Next, which means three trips out to Chicago this year. A friend said that while in town, I had to go to Grace, relative newcomer to the Chicago food scene and (finally!) Curtis Duffy's very own restaurant. I made a reservation for four on a Friday night.
The week before, four became three. Changed the reservation. I flew in the morning of, and that afternoon, my two friends had to last-minute cancel. I tried to find replacements, but to no avail. I called Grace, panicked and stressed, and the hostess graciously said that they would be happy to accommodate just me (She very thankfully didn't bring up the cancellation fee or hold me to it. I must have sounded awful on the phone.)
I dressed up, and headed over to Grace. I felt extremely self-conscious checking in, but no one reacted funnily or gave me strange looks. Here are some highlights/thoughts from my dinner:
Once seated at my table, my server asked me if I'd like any reading material; they had both the Chicago Tribune and the New York Times. This made me feel much more at ease, and as the meal progressed, I got braver and stopped hiding behind the pages.
I usually hate having my phone out during meals, but since I was alone, I was prepared to take a few photos. When I drew out my phone, my server nearly immediately brought me a little pillow for my phone. Wow.
I looked around, and really, no one was staring at me. Especially at a restaurant like Grace, the point is to be enjoying your meal with your friends. Really, no one cares.
Maybe because I was alone, or because I had brought a notebook, about a quarter of the way into my meal, my server let me know that they decided to bring me a few extra dishes so that I could try a few more things, and to not worry about eating everything. I think this is when I realized there definitely can be some good to dining alone.
Since I didn't have any friends to chat with over dinner, I spent more time talking to the servers, mostly about the food. My server kept on prodding me to ask any and all questions I had, so I learned how to puff quinoa, the nuances of the carrot dish, and why the dessert was influenced by Filipino cuisine. If she didn't know the answer, she always vowed to find out, and would return a few minutes later with the answer.
(related to the above point) I think I enjoyed the food more. There were no distracting conversations away from what was right in front of me, so I really focused on the food.
At the end of the (13-course) meal, my server took me over to the kitchen, and introduced me to Curtis (My server, to Curtis: "She finished everything." Curtis: "That was a lot of food.") Added bonus of dining alone: getting direct face-time with the chef, rather than being one of the group.
I left Grace with a chocolate bar and signed menu, floating. It was the best meal of my life. Pretty funny, because whenever people would ask me what are my favorite restaurants/meals, I'd always preface my answer with "well, a lot of this depends on who I enjoyed the meal with." Turns out my hands-down favorite meal was one I ate completely alone (Today, I called Grace to make a reservation for my next Chicago trip. I decided to make the reservation for one).
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