Aisha (2010)

This is basically the Bollywood version of Emma, the Jane Austin classic.  Ever seen Clueless?  Same type deal.  A modern retelling of Emma, where a rich popular girl loves matchmaking and upgrading her less fortunate friends.

Bride and Prejudice (2004)

While this is not really a Bollywood (it really isn't), it has some of the elements of a Bollywood.  I'll be honest, after my first film, Dil Chahta Hai, I didn't know where to look next.  I had watched it with a friend and she only gave me some vague suggestions, such as films with Aamir Khan in them ☺.