So the first thing is, it seems like a finger a better reaction from more attractive girls than less attractive, it may be an age thing but the look I got from this maybe 50 yo or so when I said she's cute. Said something similar to a young Latina and it was the opposite. It might be an age thing but just in general outside of approaching, I have better interactions with younger girls than women my age so I'm too surprised at this, this is just something to keep in mind.

Another thing is just for me personally, I have a hard time finding a good point to ask them out, shifting from casual chat to getting their phone number etc. I could try to learn flirt, or just maybe it'll come natural the more I approach. Maybe it'll come with confidence, I'm not sure