Yes, but technical side is not the most expensive and difficult thing if you are thinking about starting a bitcoin casino with safe bankroll and reasonable user interface.
If you start such a project, i think that the biggest issue about that would be to collect enough money to be safe when website plays againsts whales.

With dating sitez you dont have such a trouble. You can simply hire a coder and webmaster to start from a scratch, but all you need is good advertisment, and reasonable engine of binding people.