I've asked her out twice—once for lunch and another time for a movie. Lunch went alright, but the movie felt awkward. I want to take our relationship further. Should I keep asking her out until the awkwardness fades, or should I ask her directly if she has any feelings for me?

https://forum.lowyat.net/topic/1111256
read this first

and do NOT confess

go for activities where you can hold her hands (such as hiking, crossing the road, climbing activities, taking a walk by the beach). This gives you the natural excuse to hold her hands.

You will proceed smoothly from there once you hold her hands.

again, do NOT confess.