Throw up a nice landing signup page on olddating.com. You don't have to build the site, just have a landing page that API's to another site or just collect the leads for later or after the user signs up just have it say thanks for signing up we will notify you when we launch. Next, hire an adwords expert to send you traffic. Do like $100 a day for a week as a test. If you can land users for under $2, you will most likely make money on this assuming you convert 1:20. Then you gotta build the site and get whitelisting and a dedicated server and IP's. I would bet you that older people will rebill longer.
This is how I test ideas. It costs about 1k to test to see if it is even worth exploring more. If you cant get signups for the right price then don't even bother building the site. Once you know the landing page converts, then you build the site, once that is converting you can look into getting affiliates with older people traffic.
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