There are a gradually increasing number of things to do after work in downtown Waterbury. Here's a short list, just off the top of my head:
Mondays: live jazz at Vintage on Bank Street
Tuesdays: "Terrific Tuesdays" at the First Congregational Church on West Main Street--live music and bbq dinner
Wednesdays: Open Mic Night at Boru's
First Thursday every month: live music and refreshments at the Mattatuck Museum
Third Thursday every month: Young Professionals Networking happy hour (http://www.xyng.org/)
Plus, of course, special events like Shakesperience Productions summer performances in Library Park and whatever is showing at the Palace Theater. And the regular, every-day things like great restaurants.