My leisure travel is mainly alone. I've eaten a lot alone, and usually it doesn't bother me. I have never experienced that the restaurant staff somehow feels akward dealing with me dining alone. I normaly just ask for "table for one". I'm fine eating at the bar and sometimes prefer it.

I usually bring a book to read in. Either a novel or the guide book for the city I'm visiting. Then I can use the dinner to plan for what to see/to do the next day and look at maps to plan the best route/order to visit the places I want to see.

So, as I said, fine for having a drink at the bar; not conducive to eating a meal at the bar.

Yes, I have occasionally seen moldings which kept the food a bit too far away to be comfortable. Most notably when eating soup.

Not sure self esteem is the real issue. For example, in the case of your co-worker, I can pretty much guarantee that when she was growing up, she was told "nice girls don't eat alone in public" or something similar. There used to be a stigma attached to women dining alone (in some areas/communities) because it suggested that you were a "working girl" and looking for company. I know some of my friends heard that at home, and I'm not that old. ;)

I, on the other hand, grew up with a dad who said "Your money is as good as anybody else's; if you don't get good service, speak up!"

FWIW I have maybe twice in my life encountered attitude for being a "party of one" and I chose not to let their attitude problem become my problem.

I commented earlier in this thread that it's annoying when you tell the host/server you need a table for one and they reply "just one"?

So, I just returned to my hotel (Cape Town) with some food I picked up and went to the bar to order a bottle of wine to take to my room (which I'll also consume tomorrow night as well). BTW, I'm not eating in my room because I mind eating at the restaurant alone, I'm eating in my room because I look/feel gross from walking around all day in the sun and wind.

The bartender asks me how many glasses. His response?: "Just one glass?" Then as I'm walking out another restaurant employee also comments "Just one glass?"

So you can't win. Back to my sauvignon blanc now...

I agree with CDTraveler that entering a restaurant or bar alone is different for a woman than for a man. It has been that way all my life, and it doesn't seem to me to be any more than marginally less so now than it was ten or twenty years ago.

Bars that don't serve food are perhaps the most awkward places for a woman alone; taking a seat at a bar at a bar/restaurant is less awkward; asking for a table at a restaurant without a bar is the least awkward of the three. It helps if you dress and behave as if you're a business traveler (even if you're not). It helps to have a magazine or book (or these days, smartphone) to browse to avoid looking around and noticing that someone is staring at you.

I don't think it's an issue for women only; I know some men who say they don't like dining out alone, for whatever reasons. I'm just saying that for a variety of reasons of which men might not be aware, popping into a restaurant or especially a bar is often not as carefree and comfortable an experience for a woman who's alone than for a man who's alone.

One of my best experiences dining alone happened at a restaurant with an oval shaped bar wide enough to hold a full place mat and then some. The stools had low backs to hold a coat. There were even purse hooks under the counter. Not only was there no attitude about dining alone, I was given the option of sitting at the bar or a table. I was merely walking by thinking about where to eat. The hostess was standing in front of the patio dining area facing the street, offered up samples, talked up the menu to me and didn't blink at the solo diner request.

The bar seemed to be very social - singles, groups of two, even a group of three. The two guys in suits sitting next to me even turned around and toasted me when I received my drink.

The happy hour specials included drinks and fresh oysters. Seeing as I was front and center to the bartender and oyster shucker I had great service. This was a higher end place that formed part of a local restaurant group located in a busy shopping/business district.

For the first time in recent memory, dining alone actually caused an issue tonight. I found a place in Montreal I wanted to try and I waited about 10 minutes for a table. I got up to the front of the line and two parties of two were taken before me. The hostess apologize but stated they couldn't have a table with more than two empty chairs so I had to wait for a two-top to open up before I got sat. No big deal as it cost me maybe 5 minutes.

I'm constantly around and interacting with people. I love going for a meal alone or going to the movies alone when the need strikes. Yes, i get that i am still around people but i feel no need to interact with them other than to order

That used to be a somewhat common occurrence for me, but has not happened for at least 20 years.

This thread leaves me scratching my head a bit. I eat alone in restaurants very frequently, and I don't recall ever having an uncomfortable experience in doing so. Often I eat at the bar, but by no means always. Service has never been an issue in the least. I must be lucky!

I eat out alone both when traveling and locally. I am a relatively short woman (5'2") and find eating at the bar physically uncomfortable. I have never given eating alone a second thought and have been surprised when female colleagues tell me they order room service because they can't face eating out alone. I have had a few waitstaff in Asia push a newspaper or magazine - I actually prefer not to read while waiting for my meal. I asked a waiter in Cambodia why he was so insistent. He replied it would let everyone know I was not there looking for customers. I was 49 at the time! A restaurant host in my US home city said "Just one? That is so sad." I responded I wasn't at all sad about it and thought it was far better to dine alone than with bad company. He seemed quite surprised that I didn't agree with him.

I admire your restraint.
I would have told him where to go in two words and walked out.

My recent experiences:
One place the waitress presumed I wanted to sit at the bar (the place looked pretty full, but after when two guests came in together and she directed them to the bar and they asked if they couldn't sit elsewhere she sat there is plenty of space and led them in). Admittedly she was on the phone so couldn't really talk much other than motion with hands.
Another place there was no bar, so I sat at a table for 4 all by myself. I was wondering if the waiter was going to try to move me because a party of three came in after with nowhere to sit. But no, I guess in America they don't move you just because you don't take up all the seats.

When I've eaten alone (and I have many times in my life. Usually lunch from work, but also traveling and when I wasn't married), I haven't been bothered too much about the 'Are you eating alone?' and the horrified look of pity for the single middle-aged female who is all alone in the world. Since I AM married, I brush it off and smile. I always have a project with me, usually a book or a notebook.

I don't care for the bar option, as high chairs hurt my back and legs. I've left restaurants where the only options available are the high chairs.