Bloomington is probably the nicest place in Indiana, it feels much more modern and cosmopolitan than Indy. Broad Ripple comes kind of close to replicating the feel, but is far smaller and sometimes seems dead during the day.
Around Mass Ave in Indy is pretty cosmopolitan too, probably because it's the gay part of town.
The actual downtown scene is better than it used to be, but it's still mediocre at best.
West Lafeyette is a bunch of chains next to an industrial shithole.
Greencastle is nice, but consists of frat houses, a pizza hut, and a rock.
Don't get me wrong, Indy, including it's northern suburbs, isn't all that bad, but outside of sentimentality and a pretty small strip along the canal from Butler to Broadripple, there is really no way to tell what average midwestern town you happen to have woken up in.
Oh, Syracuse and Lake Wawasee punches way above it's weight, but only for a few months, on the weekends, when the weather is nice. It is a nice concentration of wealth and real partying.
Basically if Bloomington had an airport, and access to the damn interstate system, it would be better in just about every way than Indy.
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