Ask her if she prefers casual or upscale venues

When you ask about venue preference, you're reading whether she has thought about what kind of environment she wants to be in with you. A person who says 'I'm flexible' or 'whatever you want' is often either easygoing or avoiding the decision. A clear preference for casual, like coffee or a park or casual bar, usually signals she wants low pressure and room to talk. A preference for upscale signals she's thinking longer term or wants a more structured, intentional date. Some women will pivot your question entirely and suggest a specific place instead of choosing between casual and upscale. That's useful information too. It means she has a concrete idea and wants agency in the plan. Her answer tells you what energy she's bringing to this meeting.

Your message needs to do two things at once. First, it proposes a meetup as something that's happening, not something you're asking permission for. You're not tentatively floating the idea. You're saying 'I'd like to take you out.' Second, it actually gives her the choice between two styles without making yourself seem indecisive. The move is to name both options directly, then ask which one appeals to her. This shows you've thought about her comfort. Avoid asking open-ended questions like 'What kind of place do you like?' because that puts the burden on her to invent an answer. Instead, present the two choices. Your tone should be relaxed and clear. You're gathering information so you can execute a plan she'll enjoy, not asking for validation.

Send this message when you've moved past initial back and forth but haven't picked a specific date yet. If she replies with a clear preference, you now have the information you need to book something. If she says 'I'm easy, you pick,' reply by choosing what you think fits her personality and confirm it with her. If she doesn't reply within two or three days, send one follow up that actually suggests a specific plan instead of asking again. This shifts the pressure off her to decide and gives her an easier yes or no. If she still doesn't engage after that, move on. A person who avoids planning is telling you something about how available she actually is.