"Do you come here often?"
Really, how many times have you heard that lame line? But, it can be intimidating to open up to someone you don't know when you don't know how you will be received. It's easy to use cliche as a defense against rejection. Rejection sucks. Everybody wants to be valued and appreciated. But to be appreciated, you have to open yourself to someone so they can see something in you to appreciate. And like a novel, it starts with an opening line:
"It was the best of times, it was the worst of times, it was the age of wisdom, it was the age of foolishness, it was the epoch of belief, it was the epoch of incredulity, it was the season of Light, it was the season of Darkness, it was the spring of hope, it was the winter of despair, we had everything before us, we had nothing before us, we were all going direct to Heaven, we were all going direct the other way--in short, the period was so far like the present period, that some of its noisiest authorities insisted on its being received, for good or for evil, in the superlative degree of comparison only."
Or, for those of us less skilled than Dickens, "Do you come here often?"
Some openings are better than others. The question is; do you want to keep reading?
Conversation Starters (i.e. what you'd like to do on a first date...)
Something casual, light, and fun. Meeting for coffee, a walk through a park, maybe a lazy bike ride through the city. Something to let us get to know each other.