Hello nice to meet you too
I would suggest a slow transition just because it's harder to change dark hair to light than the other way around. (Unless you bleach your hair which you don't want). Maybe start with a medium brown and see how you like it.
Something like this
If you still wanna go dark wait a few months so you don't damage your hair too much and go a shade darker.
It's hard to tell how you would look because it all depends on the person's preference i.e. it may look good to others but not to you. Hope this helps unfortunately I don't have professional experience but I've dyed my hair a lot of times and different colors lol