New York city is a heaven for single people! I have been to New York city many times. I started going there when I had a friend who lived there because of his studies. I did New York with him many times. I then started going alone because I was familiar with the city and found out that is what I preferred. I also brought my boyfriend and though I loved going around and making him discover the city for the first time, I did not have the feeling of being by myself in that fabulous city.
Many single people, especially women, are afraid to travel alone. There is no need to worry about traveling alone. Some women fear for their safety alone and some other fear of finding being alone lonely. Don’t fear about both things! If you follow simple safety rules, like you would do in your own native city, you won’t have anything to fear. I always buy a Metrocard and take the bus everywhere, even at night. I always stay in Murray Hill and the buses leave you in front of your hotel so there is nothing to fear. If you are still skittish, take the bus and not the subway. That will probably make you feel more safe. You can cab it at night if you went out someplace that is less convenient for public transportation and you don’t feel safe.
As for being lonely in New York…I shop and sight see during the day. I often take walking tours and every time I meet people like me who are alone or like last time I met a woman and her daughter, who was around my age and a teacher like me, and we ended up chatting it up during the tour. I sensed that I could ask them for dinner and that they would have been happy to include me in their plans because the older woman, being a mother, was concerned about me being alone in the big city! Since I don’t get lonely, I did not push for dinner with them. I did another walking tour once where we ended up going out for a beer afterward. You get more occasions of meeting new people when you are alone then you are with a boyfriend.
As for eating alone…I love eating alone at the bar with a magazine. You always end up chatting with other single people like you or chatting with the bartender. I once had dinner at Campanile, a fabulous Italian restaurant in Murray Hill, and ended up talking with 2 NYPD retired cops and spending the evening there and having a wonderful time. They even payed for my dinner! Since they were well into their sixties, it was really a conversation without flirting involved.
I have a hard job, I am a high school teacher, and going to New York alone helps me take my mind off my job. I never think about the stress of my job when I am in New York. I always feel light and bubbly. Shopping and eating does that to you!