The most important part is that inline skating will prevent awkward moments, provide a few laughs, generate some thrills, provide lots of conversation starters and allow you to get to know each other better in a fun, not fake, environment. Even if cupid's arrow doesn't jab you, you'll share a good time without the forced intimacy that clubs, movies and dinners sometimes create. If an arrow does reach it's mark, you'll be hungry and tired and can sit down afterwards in a nice little sports cafe with something to really talk about.
Have you tried a skate date? Let us know how it worked out in the Inline Skating Forum!