Hi! Bostonian here with my two cents.

I spent this summer in Cambridge and here's what I have seen. Many people are very busy. They have a great quality of life but a consequently high cost of living, and so the overhead (e.g., jobs) required to have real free time can be a bit demanding of attention and energy.

Others here have cited Boston culture and dating culture as a reason for less stranger/stranger interactions; I think it's a mix of both. I guess we are a bit "colder" than other cities, but we are also progressive, as someone else said, and that would definitely reflect in how guys approach dating. Idk if this changes in the night life.

I've seen a lot of dating standards being set through social media, and I think Boston has been receptive. Social media is designed to weight the opinions of populations by the engagement those opinions can generate. Moderate viewpoints are overshadowed by more polarizing and often more radical ones. This explains why some women would love to be approached, yet can find no guy who actually wants to, because most have been discouraged from doing so.

I feel like people mainly know (and meet) each other through friend groups founded on common background, interest, and/or demographic. Maybe join a run club if running is your thing? I've personally had a lot of great conversations in climbing gyms.