Just do it. Especially if you have serious affection for them. You might get rejected, it's fine. You'll do better next time.

I was in a club today and after all that time I was involved with pickup i got a serious bonner when I saw that milf. This is fucking rare for me. I rarely feel that way.

I went to talk to her. Got rejected. Yeah sucks. But I didn't missed my chance. Night was fun anyway.