I say forget it. Not to be a debbie downer, but there's really no sense trying to build a dating social network site unless you have the technical know-how to build it from scratch or have the money to pay someone to build it from scratch.
You're not just some e-commerce store that runs off a simple wordpress template. You're a dating website. You need brand power. You need to look pretty and to function exactly like how you want it to function. You need people to be able to use the website intuitively. You're going to need the site to be tailor made to your specifications.
Wordpress and its templates are too limited for what you need. I mean, ya, they have buddy press for a forum, and a blog for... a blog. HOWEVER, the power and the functionality that you'll need for your dating website will require something built from the ground up.
Unless you want to build something scrappy and try to acquire customers first, then upgrading the site later (which will be a hindrance to your customer acquisition) you're going to need funding. I suggest polling and surveying as many people as possible to see if they'd want to be a part of this, to see if there's a need. Once you have some solid numbers, you can present them to an investor to see if they'd be interested in investing in what I can only call a SUPER HIGH RISK venture.
Dating sites are a dime a dozen, yours has to be THAT much better, THAT much easier to use for it to work. You're also going to need an active amount of users PRIOR to launch or VERY shortly after launch in order to get this thing off the ground.
Your marketing costs are going to be through the roof too.
My suggestion? Go the App route. Learn to program iphone apps and android apps. That way, you can abuse google map's tracking data or other app's check-in power. There are enough apps already built with the check-in functionality that it's not going to be super new for someone to build for you.
If you don't want to pay someone, then you'll have to learn it yourself. You said you'd be okay spending 2 years learning to program. Well get started on that. You're going to need to learn to program and you're going to need to learn at least photoshop to design the User Interface. Then you'll need to learn how to advertise and market. I say go grab Ca$hvertising and read that, it's a pretty book to start you off with figuring out your sales copy and your sales language.
Just my 2 cents.
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