Need advice for a restaurant in Worcester for a guy's night.
Vincent's is indeed a great place to hang--a hip bar that serves good, simple food (not too many choices, though). And the Boynton is good value with a lot of choices and a "good time" atmosphere. If you're up for something more restaurant-y, Flying Rhino on Shrewsbury St. also isn't bad--interesting, diverse menu and a sort of youthful feel to it.
For Italian, yes, Anthony's is still dependable. Piccolo's, across the street, is also good. Both of those places are more subdued/upscale and have less of a "boys' night out" feel than the ones mentioned above. For more basic red-sauce Italian, the Wonder Bar has a lot of character. (All three of those are also on Shrewsbury St.)
I think the Boynton would be right up your alley:
Used to be a very laid back kind of place, haven't been there in a few years.
Sort of gettig "high brow"?
It used to be certainly a guys/gals night out type of place.
There are also some good Italian places on Shrewsbury St I do believe. Just can't think of the names right now. Hope some one else will.