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Lincoln Square is older and still has a good number of German immigrants living there. Roscoe Village is either "Boystown West" or "Yuppieville" depending on who's making the description.
The nightlife in Lincoln Square is a little tamer than Roscoe Village, although neither are really big bar areas (as opposed to Lincoln Park, Wrigleyville or Boystown). There are certainly great bars in both neighborhoods, but those bars tend to be frequented more by locals. Personally my vote goes for Lincoln Square because of several of the restaurants in the area.
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