Even though many companies have been trying to crack this problem and create a good enough experience that will get main-stream adoption, nobody really has yet.
The latest company to take a stab at it is Highlight and if you believe all the buzz they've been getting since they launched a few days ago, they'll be the big winners in this space.
One of the reasons that Highlight may be a success is because of the dead-simple interface. You just install the app, sign in once, and close it. From that moment on Highlight runs in the background. Whenever there is somebody physically near you who Highlight thinks you'd be interested in, you get a notification and the app lets you message that person.
It may sound a bit creepy at first but they are putting a big emphasis on privacy to make sure people feel comfortable with what information they share, with who it's shared, and when they share it (for example you can go off the grid if you choose).
It's an interesting experience and we'll see how it will catch on. At the end of the day, like all these social apps, if they can manage to hit a critical mass of users, they'll be successful...
Highlight is free and available for the iPhone.