Coolidge Corner & Washington Square in Brookline... downtown Boston has an array of nightlife geared towards the slightly more mature crowd... it does cost a bit more, of course.
Head out to the North End for great eateries, comedy clubs and festivals; the South End for a mix of upscale and more relaxed eateries and neighborhood bars...
Harvard Square, Cambridge is also a very good place with a mix of young and old with the Brattle Theater, Regattabar and more... Inman Square with it's Jazz club, coffee houses and great restaurants...... more
Its a great time to sample those restaurants that may be outside of your regular budget. Call early for a reservation at the really popular ones (like Mistral or Davios) and be prepared to take a time that is outside of the most desirable - it may be the only way to get a table. It is well worth the effort.... more