As someone born in Manhattan who went to Penn., I liked the site, even though I have not been back in the U.S. for years. Some comments:
1) Catching and holding someone's attention on the web is tough. There is a great YouTube video on that by Sally Hogshead "How to Fascinate." She uses dating websites as an example for Internet surfers having the attention span of a goldfish. It is a "must see" for you.
2) Her video brings me to a second point. The Internet gurus maintain, with considerable credibility, that a video front and center on the landing page is the best attention getter one can have. The photograph is attractive, but just does not have "video power."
3) On line dating has, risk, risk RISK (desperately seeking Susan). Think hard about how to reduce that risk for your customers/clients. Then convey that risk removal to them.
4) Consider conducting an on-line survey of what your targeted singles want in a dating service. Your purpose is to devise a compelling value proposition for the user. "Free" may, or then again may not, be a key business driver for finding a mate on llne. People will pay a high entrance fee for the "in" club instead of going to the neighborhood pub for a perfectly good -- and reasonably priced -- drink. At the "in" club their chances (they believe) of meeting Prince Charming or Princess Supermodel are higher. I suspect that the power of premium branding also applies to on-line dating sites.
5) For this kind of venture, tieing in the social media is a must: Facebook, Twitter, Google Plus and also, I would suspect, for the upscale urban Yuppie contingent, Linked-In.
Regards, James