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As soon as your membership base hits something near the 10,000 active registrants range (this is actually a very small figure in this industry), then you can start implementing a fee for the site's services.
Whether they'll stick around or not is another story.
Many of the bigger dating sites allow their larger affiliates to rebrand their site -- that is one reason it seems like there are way more dating sites out there than there really are. I would not let anyone tell me that it is impossible to do. You might just need a different approach to get started or the funds to push a new brand into the market. I know it's a flooded market and I do have somewhat of a niche.
I couldn't tell you where to go to buy members because I don't know. I'll probably offer free memberships at first as well.
By giving everyone FREE memberships, it let's people join, post what they like, post their pictures, and start interacting with people immediately. Jewish Singles.com) and is a site for EVERYONE, then you may want to consider changing that.
Theme sites work VERY well, because it allows you to target one specific audience, instead of the entire world. Allowing new members to gain access for free, will definitely attract many more people to try your services out before they go to another place.
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This is something I thought about doing if I ever started this type of a site (which I may in the near future).