Having gone of a few dates recently, I realized that I suck terribly at driving conversation in a direction that builds intimacy and rapport.

I lost count of the times we talked about boring work-related subjects (sometimes brought up by the girl), about random trivia and other information that added nothing to the process of opening up to each other. My physical escalation is getting better with practice, but it's difficult to move forward as you talk about "what you do at your company" and other snoozefests. Been there plenty of times, it sucks for everybody involved.

I think either Sparks or Manson talk about how important it is to move towards topics that reveal each other on a more personal level, really understand what makes the other person tick. Some ideas I'm familiar with:

  • What was it like do grow up as you? What kind of kid were you? Were you awkward? Did you hate your home town? How's your relationship with your parents? What's your relationship with your siblings? If you have them, what was it like to grow up with them? If you didn't, do you wish you had them?
  • What would you do if you never had to work again? What would you spend your time on?
  • Talk about specific hobbies she has and why she's really into them, what makes them special, and how an outsider can learn to appreciate them, etc.

I could really use more ideas though. Apparently I'm a robot and I can't think of anything deep on my own, so I'm going to need your help, seddit.