and,
some of the big sites develop "characters" over time. for whatever reason. okcupid is too "goody goody, perfect people, over-educated" for him.
e.g. the user-generated questions- he interprets as social directives. He resents questions being painted into a corner. he resents their binary nature.
I agree with him mostly. It is clear that what sounded good "allow users to propose their own questions" has grown into a maze of people who claim they "like the taste of beer" or "don't". The result is the people who make it on that site are the ones who endure multiple-choice critiques and that just isn't everybody, man. People date differently.
perhaps even if you had no technical improvements, etc., but you could offer a fresh new user base of people, he would be interested. so if you try to invite people and promise them a fresh beginning - without the inertia of users of the first generation.
Also pay attention to BitCoin. it has two parallel users: miners and buyers n/ payers. Different groups take part in different ways.