The big concern I have is that you might get a date and if you look really different from your picture you're in trouble -- particularly when it involves things that you can control, like clothes.
$15 a month is cheap compared to a good tailored suit but really, the good tailored suit could be a great investment because it will help you not just look good but feel good.
As a semi-pro photographer I've thought about what kind of services guys could use in this department, my skill set can help but many guys could also use a good barber/hairdresser or a fashion consultant too so practically I'm imagining a "dream team" of 2-3 people could help somebody out to not just get a good photo but look better in general but this would probably cost a few hundred bucks not including clothes and stuff. I can see how I'd team up with a few people to serve a few customers in my town but how you make it scalable business seems tougher.
As for now though I'd really recommend photofeeler for anybody who is concerned about how they come across in photos whether it is for dating or something like LinkedIn.