ME: So... what do you like to do?
HER: (long pause) Well, you know... things...
ME: (longer pause) Oh. (even longerer pause) I like things, too...
In an effort to avoid this problem, I came up with a few things to do that would either provide for better conversation or at the very least allow me to personally amuse myself. If we were at a restaurant, for instance, I would stare deeply into her eyes like a love-struck feeb. I would then grab my drink without looking away. Still staring intensely at her, I would pretend I couldn't get the straw into my mouth, using my tongue like a physically-challenged appendage as I tried futilely to get the straw to go where it was supposed to go.
I gave myself bonus points if I could manage to get the straw to go up my nose and have it look like it was an accident.
Did this particular trick make the date a "success"? Generally, no. But that was okay, because if I was resorting to that kind of thing it was pretty clear that the chances for a second date had already packed its bags and left town for the weekend, and at least this way I got to tell a funny story to my roommates after it was all over.
On other occasions, though, when things were slow but perhaps salvageable, I would ask my date a question:
What would you like to have put on your tombstone and have it be true?
This question provoked a lot of interesting conversations. Most of my dates were caught off-guard, which at least partly the point. I wanted to see them thinking, to hear them discuss their thoughts on a subject which was inherently serious (death), and to get past some of the superficiality that often characterizes a first date (let's be honest, first dates often resemble used car pitches more than anything else: just trying to move a "lightly used" product, and to heck with honesty in the process).
Later, however, this question evolved into a kind of personal status-check for myself. After all, what would I like to be able to put on my headstone, and have it be a true statement of my life? I have my own answer to this, and periodically I will ask myself if, should I die today, people would be able to write that on my tombstone.
No, I'm not going to share my answer with you (who the heck knows what kind of creepy person you are, anyway). But I thought I might share the idea.
Ask yourself: what would I like on my tombstone?
Then ask yourself: if I died today, could someone honestly write such a thing about me?
The first is our aspiration. The second is our reality. The gap between the two is our path to greatness.