|Drawing: Josh Cochran|
Sit at the bar. Taking up a table where two or more could sit is irresponsible. Servers, hosts and bussers will not make the mistake of asking if you are expecting a guest, and it is somewhat more likely that your beverages will always be filled. A communal table setting will suffice, but only acknowledge your stranger-diner companions politely and disinterestedly. You are not there to be asked to dinner, you have taken yourself to dinner.
Pick a good time to show up. Earlier is always nice if you can stand to eat at 5 or 6, otherwise don't consider dining before 8:30 when dining alone. Earlier, you increase your risk of being somewhat ignored.
A book is an acceptable distraction. Magazines and newspapers will work, too. Just make sure that your reading material will fit discreetly next to your plate so that you can read efficiently between bites. All electronic devices should be off the table and left away. Do not text or take a phone call, nor should you wear earphones. Hopefully you have chosen a location with a pleasant enough atmosphere, not needing to block it out. Anyway, you might accidentally ignore your server when they inquire about more wine.
Enjoy a cocktail before dinner, preferably gin, whiskey or vodka based, served on the rocks. Don't nurse this drink since you're here to eat.
Kindly acknowledge any acquaintances with spare words and promise to get in touch with them another time. Follow up on your promise. If you get invited to join a table and you cannot refuse, accept only if you will be a fourth or sixth. Joining as a second, third or fifth will result in forced conversation, or the more awkward fate of the third or fifth wheel. Joining an already large party as the seventh, eighth, etc. will turn into a long, arduous ordeal, and paying the bill becomes spectacularly difficult. I prefer in all circumstances to say that I am really caught up in my book or report that I am in a hurry. If you do say that you are in a hurry, have one course, leave, and have additional courses elsewhere.
Have a bottle of wine. Do not order a half bottle or a carafe or by-the-glass. You don't have to finish it, but it's no shame if you do. Just be sure not to get too drunk since it could precipitate long conversations with your neighbors or cause you to receive too much attention from your server out of concern. Use the wine selection as an opportunity to gain trust in your server by asking for an ideal pairing.
Beer is a great alternative, but pick something with some weight to it like a porter or IPA. Never order a beer which requires fruit of any kind.
Order three or more courses, it should be way too much food but eat it anyway. Treat the menu democratically and assume that every item is a reasonable portion size such that you could eat two. You might have a traditional three course, appetizer, salad and entree, but think outside the box and consider three appetizers and an entree, or two salads and an entree. In any case, always order an entree. You are there to dine, not to snack or sample. You may have just two courses if they are both entrees.
Practice good table manners. It is a good opportunity to be civilized without having to be too serious. A sloppy solo diner draws attention to himself which is the opposite goal of a meal alone. Also, you risk losing the respect of your server, the second most important person at dinner alone.
Enjoy coffee or maybe some dessert wine after dinner, but dessert alone is slightly unsettling. You are not out to congratulate yourself for anything so don't reward yourself with dessert. If the desserts at the place you choose are too tempting, take one to go.
Tip heavy. Even if your service was basic or acceptable, it was kind of your server to accommodate the specialized needs of the solo diner. When you come back your experience might come to improve and eventually the servers will actively make sure that nothing comes between you and your night out alone.
Make it a weekly or monthly thing. You will build a rapport with the establishment and enjoy the perks of being a regular. The perks vary from place to place, but I expect you'll enjoy them.