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And zagfles idea, I like the idea of a main meal at lunchtime - I prefer a bigger meal then anyway.
It's also often much better value, especially with fixed price menus. The downside is wanting to have a lie down after a big feed when I should be out sightseeing!
I don't mind spending time on my own abroad, but I hate eating an evening meal on my own. That's the one thing that holds me back.
As others have said, dining alone isn't a big deal these days. Some city hotel restaurants even have solo diner booths where you can watch a film or use the internet whilst dining.
When I was single and sometimes travelling for work, I used to go to comedy clubs in the evening, because you can get a decent dinner and everyone's looking at the stage. Also used to go on organised walks of the city in the evening, particularly ghost walks in some locations, because they're usually hilarious and interesting rather than boring or spooky.
Biggest bugbear I have with traveling solo is the "single supplement" charged on rooms. As a result, I'll often take a tent and camp instead. Not so easy with city breaks.
I can't remember the last time I paid a "single supplement" on a hotel room. Book direct with the hotel and you will just pay the standard room rate regardless of how many people are in it and some with give a single occupancy discount.
Of course that means that a single person will pay twice what a couple pay each for a double room (assuming they split costs) but that's the same as getting a taxi.