First date conversations can be rough; here are some softballs.
I'm not sure that there is any actual data to support this, but first dates are the most stressful moment in a person's life. It doesn't matter if you like the person or not, it is crucial that they like you. Unless you're one of those types with an unhealthy level of self-esteem, self-awareness and self-love, you have probably felt a crushing amount of anxiety at the prospect that someone wouldn't immediately think you're the cat's PJs*.
The good news is that you've already made enough of a first impression that this person agreed to a date with you (unless it's one of those blind dates and that's an absolute crapshoot even with the best of preparation). Some people say that certain topics are off-limits for first dates and I some merit in that assertion. Which leaves you with doing stuff and small talk as the only the only way to interact.
You may think small talk is just a bunch of petty chit-chat but it need not be an exercise in abject banality. You can learn a decent deal about someone with largely innocuous questions and decide if you're up for sharing more important stuff plus this could give some hints at future gift ideas. Don't be a jerk about it, slide these in there casual-like. And, like any good investigatory journalist remember to infer "why."
- "If you were to be trapped in an elevator, who would you like to be with? Present company excluded, of course."
- "Do you have siblings? If so, how many and what order were you born?"
- "Have you ever been to [insert your favorite travel destination that's not synonymous with prostitution or drugs]?"
- "What's your favorite word?"
- "What skill [or super power, if you're frisky] that you do not possess would you most like to have?"
- "What's your favorite thing about yourself, non-physically**?"
- "Would you like another drink?"
In virtually no circumstance should you ask if you sat in some gum and then expose yourself.
*Note: Hooking up then going on a first date seems like decent way to assuage a little discomfort, it's a forcefield.
**Note: Specify non-physical, if I had a nickel for every time I heard "breasts," I would have more money than I do now.