It's funny how the University has this reputation as a grind school, a place where you can't have any fun. While it certainly can get dreary in the winter, when you go for weeks without any sun coming through the silver sky to brighten the gray fake gothic buildings, I didn't find that that kept people from dating.
On the contrary, most of the people I knew in college were fairly settled into stable-ish relationships through the long, cold winter. It was only when spring came, and the grounds crew were planting beds of crimson tulips on the quads and the warm, brief days gave way to orange nights that those relationships shattered and people went into an orgy of dating. Nobody gets much work done in spring, and there's always a run on Bond Chapel for spring weddings for alumni. And the summers...
You do have to work at Chicago. There's an atmosphere of intellectual challenge and excitement that can be both inspiring and exhausting. I met professors who encouraged me (like the incredible David Bevington, Shakespeare scholar extroardinaire) and professors that terrified me. Michael Murrin convinced me by his very brilliance that I could never be an Arthurian scholar, because there was no way I would ever know half as much as he already did. He'd undoubtedly be unhappy to know that, as he has a passion for his work and a love for passing knowledge on to others.
Chicago is very much a place where people care passionately about learning, about knowledge. As such, it's a place I cherish now that I'm out in the real world. It does seem very much an ivory tower, but a precious one...