I'm not seeing your solution to the chicken and egg problem here.
I'm not seeing your solution to the chicken and egg problem here.
In theory, the site could function with just two users.
Then with luck the membership should grow by word of mouth.
Matching people DOES require a huge amount of people to stand the chance of finding a geographical and personality match. This idea of date oriented meeting seems to nail the first problem perfectly.
@OP: I think it's got legs, serious legs. Though I see a problem with no-shows (I guess the 3 or 4 "couples" per date fixes that somewhat). The question is how do you monetize?
It's also possible that local restaurants/attractions could sponsor certain dates (i.e offer kickbacks), but the site would have to be sending a LOT of dates per week to any given place for those kickbacks to materialize.
A third idea might be to take the community of active daters you have created and host paid events periodically. For example, for users who enjoy nightlife, you could have a blowout bash with a cover charge. For users who enjoy classic movies, you could have a wine tasting and a screening of a classic movie.
I'm sure there are better ideas out there for paid events, but you get the idea.