Some nice areas in BPT (e.g. Black Rock)

If I were young and starting out, I’d rather live by myself in Bridgeport than with a roommate in Stamford.

Every city has bad areas.

If not dead-set on city life, Milford, Stratford, Shelton are all nice places to live. Commute to Stamford sucks, though, if that’s where you work. Ditto from Bridgeport. 30 mins is your absolute best case scenario.