#18: Plenty Of Fish Sold For $575M

Summary: Plenty of Fish is one of the most popular dating websites in the world. The site was just sold for over half a billion dollars to Match Group, the company that owns both Tinder and OKCupid. Plenty of Fish sold for $575M and its owners are reeling in the success of the site. The site has been around for a long time, but is not exactly the best when it comes to matching people. It feels more like "Here are some people that live near you, you should date them." Maybe with this sale, we'll see a better matching system but as far as free sites go OKCupid seems to be the at the top of their game.