to the world at large you can do it, but you'll need some decent software. The application of choice is a delicious program called Sam2 Broadcaster, which does exactly what you want to do - it's described as "A radio station in a box". I've seen Sam2 at work, and it's worth every penny of the $200 it will cost.
You'll need to invest a fair bit of time on this project if you want it to run professionally, and don't forget that it's illegal to broadcast copyright-protected music unless you pay the performing rights fees.
You might also find that NTL st up and take notice if you have an audience of any size - because you'll start to consume a fair chunk of bandwidth.
Apart from that........
Keep a close watch on your site's content - don't let it cross the thin line that separates the OK dating site from the definitely not OK dating site - I'll be watching as long as you have your link posted here, and I'll remove the thread if I see anything untoward.
The better managed your site is, the more business you'll attract. Allow it to degenerate in any way and you'll have a complete failure on your hands.