may be i'm asking a stupid question but can someone clarify what is the chicken and egg problem with dating sites?
It's difficult to attract people to a dating site that has very few members. You have to implement a non-tech solution, such as a huge mass-media advertising campaign (e.g. Dating Direct have ads in the breaks in Gray's Anatomy), which is hugely expensive. Or you have to have a viral idea, like OkCupid offering quizzes to LJers and getting them to create profiles as an aside.
Since I have no specific familiarity with dating sites, all I could suggest was a vague, general approach. Of course a big dating site might have a lot of money to advertise, but a small one probably can't afford it. But that's obviously one possible way to get some users.