Hey there,
Fellow UNC undergrad alum...2001. Took a year off to get residency, and then went to Carolina for dental school.
I loved Chapel Hill and it was wonderful to spend more time there. It didn't get old...but it does get different. Although I obviously didn't go out like a rockstar in dental school compared to undergrad, I did frequent different places. Top of the Hill, Martini Bar etc got a little bit old and a little bit young. I went out a little more out towards the West End...wine bar, green lantern, although we did hit up ToTH somewhat. I enjoyed dental school there and really just being in Chapel Hill. I miss it like crazy.
Good luck.