For the life of I can’t figure out how to keep somebodies interest before the first date. Applicable to texting and apps.

Every time I match or start texting someone, I try to ask fun smart questions but they fizzle out quickly after.

I get the standard you want to ask meaningful questions like if they have a hobby ask about it. I get a short description and then what? Then don’t describe it passionately, they don’t follow up about asking about mine, nor do I have any clues on how to continue.

I’m not trying to be friendly but I’m also not trying to be creepy by flirting with them fight off the bat.

I find I have ~5 to 10 short messages back and forth before they give up with responding. If I send a long text, they are less likely to respond.

I have no issues if they are 100% into me but often I am not into them.

What are your thoughts? Can you provide a few hints?