Not that big of a deal.
I've probably eaten by myself at fine restaurants close to a hundred times over the last 10 years, both as a business traveler who didn't want to miss out on U.S. cities' acclaimed restaurants by eating only room service, and as someone who just doesn't love to socialize all the time. I'm engaged now and I can think of several recent restaurant meals I ate alone, all very pleasant. (Technically, yesterday, I brought my dog.)
A few reassurances:
Servers don't care that you're by yourself. I've been a fine dining server, and no other servers ever said anything bad in my presence about single diners. (Well, only if they were a regular who never tipped well.) Most people who eat by themselves bring reading material -- I always have a New Yorker next to my place setting, for example -- so they're self-sufficient. There's no reason to feel guilty about taking a table for two for just yourself, either, because the table next to you might be ordering salads and water while you're having three courses. Basically, servers like people who are nice, and low-maintenance, and excited about the dining experience, so service for single diners tends to be really, really good. Recently, a server at a nice French bistro decided the restaurant must be too dark for me to read, so he dropped off a second candle for my table and didn't even say anything. Loved it. I always end up tipping at least 20 percent when I'm by myself. (If you're alone and eating at an inexpensive restaurant, it's a good idea never to tip less than 5 dollars.)
Who cares what other diners think of your eating by yourself? Really. I was once eating at the bar at a hot new seafood restaurant in Atlanta on a Friday night, in town for a wedding, and another woman my age waiting for friends said to me that she could never eat out by herself, in that judgmental way. Meanwhile, the bartender was pouring me the dregs from the cocktail shaker of nearly everything he was making, and giving me tastes of wine. (Did I mention the service can be really good?) Sometimes adjacent diners will start chatting with you, especially if you decide to eat at the bar, and it's up to you if you want that to be part of your experience. I'm usually not in the mood, so I'll request the restaurant's tiniest two-top table.
The kitchen probably doesn't care. I've often ordered three or four appetizers and requested that they be coursed (coming one after the after) instead of the linear appetizer-entree-dessert route, just to be able to taste more things on the menu, and no one has minded, or at least let me know they mind. I will say, the small plates trend of just sending dishes out as they're ready drives me crazy, because it means dishes pile up and get cold, and I feel rushed. So if you want to go to a small plates restaurant, chat with your server about coursing your meal. There's only one of you, one dish at a time.
The manager cares a little. Maybe try to get your reservation not at the restaurant's busiest time, or if it's no-reservations and you arrive and they're clearly slammed, offer to eat at the bar. Managers are very concerned with large parties and filling seats.
You're guaranteed to have a good time. You like hanging out with yourself in other contexts, right? This is the same thing as shopping, exercising at the gym, or getting coffee by yourself. You exchange pleasantries with staff but go about doing your thing. Bonus, no one can mess up your dinner by bringing up a sensitive topic or making a scene over a whole fish arriving with its head on. (The collar is the best part. Obviously.)
(Little addendum: if you bring a notebook and act like a critic -- which is not even what real food critics do -- as someone else recommends, your server and the manager will absolutely not like it. Trust me, you want to win over the staff.)
April 2008. Chicago.More questions on Restaurants: