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The past two days I've mostly been working on writing dialogue, which is more difficult than I anticipated, in the sense that it's not coming as naturally as I'd expected. I want to display the awkwardness of speed dating as well as make the conversation natural and interesting (right now I'm mostly failing at the 'interesting' part).

I think I'm also setting the bar way too high for myself for this being my first game. Oh well.

It may help you to plan out each session of speed dating. It doesn't need to be complicated just what's the personality of the date, their major interest and what they do. Then you'll be able to quickly write what you think they'd be saying during a date.

I've been trying to do exactly that and it has been going a little smoother. Thanks!