I've lived in the following cities:
* New York. Overall, a fantastic place to live if you can afford it. I spent 7 years of my life here. Slightly more single women than men tilts the balance and makes this city a guy's market. Hook-up culture, this is a great place if you want to have lots of short relationships and ONS, but the downside is it's always so easy to say "next" and find another partner that it can be hard to form stable long-term relationships. Lots to do. However, it does eventually get old, and the bitter long cold winters, sauna-like summers, pollution, very high cost of living, very high tax rate especially in the city, etc., drive most people out after a few years. Good place to live for a few years, then move somewhere quieter. Can seem over-hyped if you have been here too long. Yes, it's the Empire State Building - so what? It's not like other cities don't have nice tall buildings with pretty lights.
* Boston. Very cold winters. Great for college students but not a great place to live as a single adult. It's hard to break in to the college scene. "Town and gown" phenomenon, are you an academic or a Red Sox fan? They don't get on so well. Good public transport is about the only thing going for this city. Anyone with a brain goes to NYC to party over the weekend, hence the half a dozen bus services, but it's a long trip.
* San Francisco. It's all about the H's here. Hills, hippies, homeless, homosexuals. If you are gay or Asian, and you are flush with cash, this is a great city to live in. If you work in tech and are in your 20s, you might just have to live here. Otherwise, it's very poor value for money and you are better off elsewhere. The presence of tech attracts lots of men, and there are too few women to go around, so the men are constantly trying to out-peacock each other to get girls. Most of the girls here are already in relationships, and the ones that aren't are not necessarily ones you'd want to date. It never really gets warm and most evenings it is cold. You always need a jacket. It gets windy because it juts out into the sea. The entire city reeks of pot and piss, no matter where you go, at all times of day. The public transportation sucks. Oakland or Berkeley are better options but they are small, and people go to the city to party, but the public transit shuts down early so it's hard to get back without shelling out $30 for an Uber. Traffic is now terrible at all times of day, even worse than LA. Did I mention CA state taxes are through the roof. No thanks.
* San Diego. What a beautiful city - perfect weather. If you enjoy being outdoors, being on the water, or going to the beach, this is a great city to live in. Lots of retirees and ex-military types. Expensive but good value for money, for the most part, compared to SF etc. Girls are easy going and fun loving (I didn't date here much so I can't speak to that). Traffic isn't too bad. Public transport not great, but driving is easy. Nice downtown area with good apartments, walkable. Some nice fun areas like Hillcrest. Main downside is, there isn't much to do here, and it gets boring; people talk about going up to LA to party, but the long drive and bad traffic in LA put people off actually doing it. People also talk about partying down in Tijuana, but it is an absolute sh*thole so people don't. CA state taxes apply.
* Los Angeles. What a hellhole. Where do I start. The main misconception people have about LA is that they think it's a city. It isn't - it's a bunch of cities in close proximity connected by extremely congested freeways. Some of the cities are extremely nice, e.g. Santa Monica, but others are dumps or places you are scared to set foot. Good weather but the air quality is bad. Lots of aspiring actresses here, some of them quite good looking, but honestly it's depressing to date them and put up with their superficial airhead "I'm gonna be a star" attitudes while watching them earn no money waiting tables and get rejected from every audition they ever go to. LA has become very expensive thanks in part to tech companies setting up here (e.g. Snapchat) and it's not good value for money. Spending three hours a day watching tail lights and inhaling exhaust fumes is not anyone's idea of a high quality of life.
So between the cities I've lived in, it's got to be New York. But as someone who did the NYC grind for 7 years and is ready to get out, I'm now looking at Florida (probably FLL or Tampa), Austin TX, and watching this thread for more ideas.
* New York. Overall, a fantastic place to live if you can afford it. I spent 7 years of my life here. Slightly more single women than men tilts the balance and makes this city a guy's market. Hook-up culture, this is a great place if you want to have lots of short relationships and ONS, but the downside is it's always so easy to say "next" and find another partner that it can be hard to form stable long-term relationships. Lots to do. However, it does eventually get old, and the bitter long cold winters, sauna-like summers, pollution, very high cost of living, very high tax rate especially in the city, etc., drive most people out after a few years. Good place to live for a few years, then move somewhere quieter. Can seem over-hyped if you have been here too long. Yes, it's the Empire State Building - so what? It's not like other cities don't have nice tall buildings with pretty lights.
* Boston. Very cold winters. Great for college students but not a great place to live as a single adult. It's hard to break in to the college scene. "Town and gown" phenomenon, are you an academic or a Red Sox fan? They don't get on so well. Good public transport is about the only thing going for this city. Anyone with a brain goes to NYC to party over the weekend, hence the half a dozen bus services, but it's a long trip.
* San Francisco. It's all about the H's here. Hills, hippies, homeless, homosexuals. If you are gay or Asian, and you are flush with cash, this is a great city to live in. If you work in tech and are in your 20s, you might just have to live here. Otherwise, it's very poor value for money and you are better off elsewhere. The presence of tech attracts lots of men, and there are too few women to go around, so the men are constantly trying to out-peacock each other to get girls. Most of the girls here are already in relationships, and the ones that aren't are not necessarily ones you'd want to date. It never really gets warm and most evenings it is cold. You always need a jacket. It gets windy because it juts out into the sea. The entire city reeks of pot and piss, no matter where you go, at all times of day. The public transportation sucks. Oakland or Berkeley are better options but they are small, and people go to the city to party, but the public transit shuts down early so it's hard to get back without shelling out $30 for an Uber. Traffic is now terrible at all times of day, even worse than LA. Did I mention CA state taxes are through the roof. No thanks.
* San Diego. What a beautiful city - perfect weather. If you enjoy being outdoors, being on the water, or going to the beach, this is a great city to live in. Lots of retirees and ex-military types. Expensive but good value for money, for the most part, compared to SF etc. Girls are easy going and fun loving (I didn't date here much so I can't speak to that). Traffic isn't too bad. Public transport not great, but driving is easy. Nice downtown area with good apartments, walkable. Some nice fun areas like Hillcrest. Main downside is, there isn't much to do here, and it gets boring; people talk about going up to LA to party, but the long drive and bad traffic in LA put people off actually doing it. People also talk about partying down in Tijuana, but it is an absolute sh*thole so people don't. CA state taxes apply.
* Los Angeles. What a hellhole. Where do I start. The main misconception people have about LA is that they think it's a city. It isn't - it's a bunch of cities in close proximity connected by extremely congested freeways. Some of the cities are extremely nice, e.g. Santa Monica, but others are dumps or places you are scared to set foot. Good weather but the air quality is bad. Lots of aspiring actresses here, some of them quite good looking, but honestly it's depressing to date them and put up with their superficial airhead "I'm gonna be a star" attitudes while watching them earn no money waiting tables and get rejected from every audition they ever go to. LA has become very expensive thanks in part to tech companies setting up here (e.g. Snapchat) and it's not good value for money. Spending three hours a day watching tail lights and inhaling exhaust fumes is not anyone's idea of a high quality of life.
So between the cities I've lived in, it's got to be New York. But as someone who did the NYC grind for 7 years and is ready to get out, I'm now looking at Florida (probably FLL or Tampa), Austin TX, and watching this thread for more ideas.