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Boston has a great bar scene. Our bars and restaurants are regularly recognized as some of the best in the country. We also have many, many bars for such a small geographic area. IMO the bar scene in Boston is superior to SF.

These are the real pain points for living in Boston as a 20-something:

The T is miserable, always. The weather is miserable, 9 months per year. The attitude is cynical, usually. Massholes are real. Prices are high. We spend too much time comparing ourselves with NYC.

Otherwise, Boston is excellent. The city is clean. People are educated. Some are even attractive. The bike sharing is great.

Bar closing time is not a real issue. It's just a symptom of an old-fashioned, stuck in its ways, puritanical city.

[rradu]

Agree with your first two points, especially in the comparison to NYC. They're just not comparable from the outset--NY is way bigger (469 sq miles and 8+ million residents, while Boston is 90 sq miles and 600,000 residents).

But I'd say bar closing time is a real issue. I hate having to end my nights at 2, especially if I have to cab it back anyway because the T isn't running.

Actually, that's what I'd say the biggest issue with Boston is--the T service. Not only does it suck when it is running, it doesn't even run when I need it the most. The MBTA is very poorly-managed and many hundreds of millions of dollars in debt (very few actual improvements to the system are done because of this; it will take the MBTA until ~2050 to pay back all its debts under the current structure assuming it incurs no other expenditures)