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I would avoid the "fact based" small talk (where are you from, what's your job, etc). I would not even tell about it, unless it is critical to the plot. I'd just dismiss that as five minutes of awk...
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#3: Attribution notice added
Source: https://writers.stackexchange.com/a/31765 License name: CC BY-SA 3.0 License URL: https://creativecommons.org/licenses/by-sa/3.0/
#2: Initial revision
I would avoid the "fact based" small talk (where are you from, what's your job, etc). I would not even tell about it, unless it is critical to the plot. I'd just dismiss that as five minutes of awkward biography before we came to a real question. As a general rule, **_always_** make your dialogue contested, challenged, conflicted, whatever you want to call it. That is _interesting_ to read about. Even in a first date situation, isn't it best when you get into friendly debate (on some topic you aren't going to get angry about)? Isn't what is interesting about somebody the attitudes or likes or dislikes you wouldn't have expected? The funny stories of their childhood acting career? The haircut they now find the most embarrassing? What is the dumbest compliment you ever gave a date? What fruit flavor do you hate the most? Some of these are conflicted as _challenges_ to reveal information the other may not wish to reveal, which can create some real conflict, light-hearted conflict by a refusal to reveal or changing the subject. Of course, if the first date is to go badly, somebody misreads these attempts to find some humorous common ground as **interrogation** and shuts down; then the conflict is more real and harsh: I'm not having fun and want to leave; this guy/girl is being too nosy; or too crude or too insulting. Negative tensions are easier, positive tension (friendly verbal wrestling) is more difficult, but should be possible if you built your characters to like each other. Always try to keep some tension in your dialogue, the tension is conflict. If you want the date to go well, the tension is light hearted and funny: _I'll show you mine if you show me yours,_ but as that applies to worst date, shortest date, dumbest venue, or whatever else has happened in their lives. If the romance is central to the plot, some of these answers can be put to good use later in the plot, for humor or serious purpose (she really DID get to know something personal about her date that helped her find him, for example.)