My experience - I dated quite a bunch of girls from dating apps.
Usually i chatted with them for like 3 days to 1 week before asking them out.
Things to note: IF they agree to go out with you, then you already have high chance.
Surprisingly, most girls don't mind to have fun if you can get close and click with them. They know what they sign up for when they use dating apps.
I never confess, things will flow naturally.

There are many fishes out there. Dont be afraid to fail. There is always the next one out there.