When I was living in Budapest and working for a company in London, I'd spend about a week of every month living in the company flat just off Kensington High Street. Alone. (generally) It's a rather swanky area. I was making good money. And dining alone was fun sometimes (especially at wagamama, because you are never alone at wagamama!), but after a while it got a bit lonely. So I would walk up to random people that caught my interest, and invite them to have dinner with me, on my tab. Actually ate with two mildly famous supermodels. A young couple from Holland. London locals, etc. It was fun and fascinating! Eating dinner alone is a privilege, not a burden. You become vastly more interesting to the staff and you have an experience that's all about you.
I have no compunction whatsoever about dining alone at any level of restaurant and have often ended up dining with others as well. I think it is great fun. I sat at the bar of a swanky Montreal resto once, for the 8 course tasting menu, and the staff set me up with what was essentially a dinner party with Linda Evangelista, Kyle McLachlan, former Canadian Prime Minister Mulroney and his wife.
It was interesting! And fun. Odd thing is, just like most nice strangers you dine with, we only talked about casual bullshit, they were all very nice and it was a great couple of hours. Mostly kudos to the staff in that instance. They were tipped well that evening. After my second course at the bar they had set a table set for me and insisted they would be by to chat regularly if I wasn't busy. I thought that was an odd thing to say. They put me at a deuce between two 6 top tables in a VIP-ish area which I also thought a bit odd. After about a minute my next course was brought out and the waitress sat down and chatted for a few minutes then "Kyle and Linda" were seated to my left. I gave them a nod and a hi, kept eating and then got out this furniture book of stuff that I was thinking of buying. Kyle noticed and asked me about it. We chatted about that for a few minutes and then I saw former PM Brian and Mila being seated at the table to my right. I stood up and said "Good evening Mr. and Mrs. Prime Minister." Not sure if that was kissing ass or not but he was former head of state so... I had just came from the train station and still had my lawyer's briefcase with me but tucked under the table. As he was sitting, Mulroney must have noted it and made some joke about me probably being a labour lawyer like him. We had a chuckle about that and for some reason I turned to my left (they were already looking) and asked "have you met Canadian supermodel Linda Evangelista and American super actor Kyle McLachlan? This is PM Brian Mulroney and Mrs PM Mila Mulroney." Then we just talked about who knows what. No grand design. That is the first and only time in my life I have ever acknowledged that someone is "famous". In my experience, conversations are better when you just talk to others as they are "normal" people and not who you/they are "supposed to be". That's also how Charles Barkley decided to buy me a few glasses of scotch! :) Longer than expected reply. Oops.