The scenario where Upcoming excelled, or at least the one that that seemed to "convert" users and why I think 10yrs later it's still so fondly remembered (looking at the response on Twitter has been nice) is when Upcoming told you about that event that you didn't know about and would have kicked yourself for missing ("if only I had known this thing I would have loved to go to was happening last night!").
Over the years I experienced this first hand many times (regrettably, also a lot of "can't go, too busy working on Upcoming"), but I haven't seen anything since that's provided the sort of social+interest-based serendipity that Upcoming did in its heyday. A lot of times in the past few years when I've been traveling I've wish there was something like Upcoming that could recommend the most interesting things to do in a city that night (like 4SQ or Yelp for events).
Over the years I experienced this first hand many times (regrettably, also a lot of "can't go, too busy working on Upcoming"), but I haven't seen anything since that's provided the sort of social+interest-based serendipity that Upcoming did in its heyday. A lot of times in the past few years when I've been traveling I've wish there was something like Upcoming that could recommend the most interesting things to do in a city that night (like 4SQ or Yelp for events).