If you're the type of person who would wear Glass on a date, the chances are the type of person who would date you would also be a big nerd. They might be interested or even turn up wearing Glass themselves! Maybe Glass is how you got talking to each other in the first place, I imagine if two wearers see each other they often say hello.
It rather suggests only men would wear Glass, and no women are nerds, or want to date nerds, which is hardly the case and is actually kind of sexist. Some of the biggest nerds I know are women.