Single (or formerly single) online daters of AW who seek a relationship, how often do you go on first dates?

A few different reasons. It might sound very anti-me to say this, but I get the feeling he wouldn't be into being hit on first... he just seems a bit more traditional, which doesn't bother me because I honestly kind of prefer being pursued/hit on first. I wish it wasn't like that, but it is what it is.

I do know that a lot of women hint their interest at men in very obvious ways in order for the guy to get started. I'm not sure how else to do it at this point. I'm really nice to him, but kind of playful.. in person and via text. But I can't push it too far or flirt too hard. We're not colleagues but we kind of work together in one aspect, so I don't want to ruin our "professional" ties if it doesn't seem mutual.

He snaps me, always gives me his opinion on things I need help with, has actually helped me out before (I got into a minor accident and he drove me around and made sure my car was fixed and everything), so I know he's a good guy who cares about me to a certain extent. I just don't know how much he cares. We're going on a (professional) trip soon though so maybe that'll help clear things up? He extended the travel together offer to a few of us but was keen on having me travel with him and his friend, so we'll see.

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