When I first started traveling for business, I was petrified of dining alone. I thought I would be marked as a loser and I had no idea how I'd fill my time. So I bought take-out or ordered in room service, which sometimes worked OK because of the quiet or the chance to get out of my work clothes. But night after night -- what a drag.
When I started venturing out, I took a book or a couple hours' worth of magazines or newspapers and headed for the 
hotel's everyday restaurant or a nearby non-descript eatery. I was completely self-conscious and chose an obscure booth or table, trying to look occupied, self-possessed, or in a hurry, as if eating was part of the day's frenetic continuum of a busy person, something to be endured. Soon I realized how dumb I was because, as a foodie, I'd rather not eat at all than chow down average food and blah wines.
In phase three, I got up the courage to go to fine restaurants -- but schlepped along all that reading material. That was sheer comedy. How tacky to place a newspaper or magazine on a white table cloth beside a lovely place setting. How impractical to try to read a book with salt and pepper shakers or a sugar bowl holding the pages open while I cut and eat my food. How insulting, finally, to the chef, the servers, the other patrons, and, in fact, me to gallop through the meal without the slightest enjoyment and most likely drawing the attention that I was hoping to avoid.
I pushed myself and started going to fine restaurants -- and in the process began to discover the real pleasure of dining alone. I'll never forget the first time I spent $100 on myself for a meal at Vong in Manhattan's East Side. It was like having treated myself at a spa. I was liberated after that.
Not all restaurants are appropriate for dining solo. In part, that also depends on your personality and in what environment you are most comfortable. But my conversations with chefs, bartenders, servers, house managers, and other solitary diners have led to these guiding principles for having a great solo dining experience. Read on, and send me your favorite solo dining places. Stay tuned -- I've a forthcoming list for you as well.
Solo dining essentials:
- Don't load up with reading material. Watch the show around you.
- Sit at the bar -- at least in nicer white-tablecloth restaurants. You can talk to the bartender, those around you, or no one (and listen to others' conversations). The bartender usually knows everything about the kitchen, the chef, the owner, and the popular specials. (This is not recommended for pubs and noisy hang-outs, or smoky establishments.) I've been set up with a cloth mat, a votive candle, even a little flower in a tiny vase, to replicate the experience of the diners at the tables. And the service is great.
- Choose sidewalk tables on a busy thoroughfare. The people-watching can be as engaging as a pricey Broadway show. A woman alone is visually intriguing -- particularly one who is staring back.
- If you really need to have company, choose restaurants with a community table.
- Recognize that some restaurants discourage (subtly) solo dining. Looking at the economics, it deprives them of half their income for those 1-2 hours at your table. Ready for that, a friend once told me she typically makes reservations for two, but when her companion "didn't arrive," she decided to stay and have dinner alone.
- Appreciate the advantages of a fine meal in solitude, and enjoy the freedom of your own company. Some of the companions I've had, I would have rather been eating alone.
