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Small-Scale Question Sunday for May 7, 2023

Do you have a dumb question that you're kind of embarrassed to ask in the main thread? Is there something you're just not sure about?

This is your opportunity to ask questions. No question too simple or too silly.

Culture war topics are accepted, and proposals for a better intro post are appreciated.

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If you're bantering back and forth, you're already in a good spot. There's two ways you can go.

You can ask something where there's obvious subtext, like "we should get coffee/dinner sometime", or make it even more strong by actually setting up a specific time to get coffee or dinner. This was how I asked out my now wife, and at least a couple previous girlfriends. Of course, I also failed with this many times, too. You can do this if you feel you already have a good enough rapport such that she probably already likes you, or if she thinks highly enough of you such that she would be flattered by you asking her out, not weirded out.

Alternatively, you can try to start setting up social engagements with groups and include her in them. This is safer, and you can use it to keep building rapport, but eventually you'll probably have to try to "ladder leap" by doing the first thing anyway.